text
stringlengths 0
7.07k
| input_ids
sequencelengths 0
1.6k
| attention_mask
sequencelengths 0
1.6k
|
|---|---|---|
[] | [] |
|
= = Original design = =
| [
296,
296,
55211,
45717,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The Type 1 gold dollar depicts a head of Liberty , facing left , with a coronet or tiara on her head bearing her name . Her hair is gathered in a bun ; she is surrounded by 13 stars representing the original states . The reverse features the date and denomination within a wreath , with the name of the nation near the rim .
| [
20996,
29937,
284,
30989,
45774,
51435,
332,
31060,
4706,
50395,
279,
45949,
31269,
279,
32487,
332,
38117,
1859,
4715,
4806,
7032,
4712,
21811,
31060,
51016,
21811,
31496,
281,
20035,
31039,
4600,
56300,
4596,
332,
21397,
294,
22464,
4600,
62621,
4450,
3486,
39800,
64552,
22590,
56778,
47398,
281,
20996,
52748,
56215,
22590,
30580,
21265,
51427,
33944,
47806,
332,
22782,
7067,
279,
32487,
22590,
31496,
4706,
22590,
46640,
31503,
22590,
22390,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Contemporary reviews of the Type 1 design were generally favorable . The New York Weekly Tribune on May 19 , 1849 described the new dollar as " undoubtedly the neatest , tiniest , lightest , coin in this country ... it is too delicate and beautiful to pay out for potatoes , and sauerkraut , and salt pork . Oberon might have paid Puck with it for bringing the blossom which bewitched Titania . " Willis ' Bank Note List stated that " there is no probability of them ever getting into general circulation ; they are altogether too small . " The North Carolina Standard hoped that they would be struck at the Charlotte Mint and circulated locally to eliminate the problem of small @-@ denomination bank notes from out of state . Coin dealer and numismatic author Q. David Bowers notes that the head of Liberty on the Type 1 dollar is a scaled @-@ down version of that on the double eagle , and " a nicely preserved gold dollar is beautiful to behold " .
| [
64182,
52749,
4706,
22590,
29937,
284,
45717,
32462,
59758,
59705,
281,
20996,
20512,
30074,
45050,
50752,
4712,
20394,
3492,
279,
3491,
669,
59488,
22590,
22168,
45774,
4423,
269,
63962,
22590,
31504,
7513,
279,
22601,
25728,
279,
38895,
7513,
279,
30474,
4596,
32234,
51337,
19312,
4601,
4600,
22614,
55947,
21265,
59219,
4811,
22269,
22249,
21700,
56897,
279,
21265,
22437,
7494,
2151,
2244,
279,
21265,
31935,
31729,
281,
29504,
2098,
39021,
31059,
31612,
4138,
1794,
32487,
4601,
21700,
55660,
22590,
37871,
2097,
40186,
21350,
41710,
37465,
1937,
281,
269,
45057,
274,
28460,
29492,
29290,
47397,
32227,
269,
39934,
4600,
4692,
63787,
4706,
32229,
30789,
51844,
31162,
51832,
63338,
294,
32232,
21286,
61566,
22614,
39720,
281,
269,
20996,
37094,
54895,
55341,
38709,
32227,
32232,
40219,
4435,
47437,
4424,
22590,
58736,
29401,
21265,
61677,
52150,
4811,
59606,
22590,
52569,
4706,
39720,
299,
46,
65,
51427,
33944,
30230,
39141,
30917,
22249,
4706,
39802,
281,
28665,
45667,
21265,
22196,
25956,
8807,
45242,
316,
47,
36558,
19538,
7500,
39141,
32227,
22590,
31060,
4706,
50395,
4712,
22590,
29937,
284,
45774,
4600,
332,
47180,
299,
46,
65,
30678,
53275,
4706,
32227,
4712,
22590,
45786,
38327,
279,
21265,
269,
332,
46665,
60240,
30989,
45774,
4600,
59219,
4811,
45291,
269,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Modifications = =
| [
296,
296,
29411,
25418,
27168,
116,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
Mint records indicate the first gold dollars were produced on May 7 , 1849 ; Longacre 's diary notes state instead that the first were struck on May 8 . A few coins in proof condition were struck on the first day , along with about 1 @,@ 000 for circulation . There are five major varieties of the 1849 gold dollar from Philadelphia , made as Longacre continued to fine @-@ tune the design . Mintmarked dies were sent by Longacre 's Engraving Department at the Philadelphia Mint to the branch mints at Charlotte , Dahlonega ( in Georgia ) , and New Orleans ; coins struck at the branches resemble some of the types issued from Philadelphia , depending on when the dies were produced . Of the coins struck at the branch mints in 1849 , only pieces struck at Charlotte ( 1849 @-@ C ) exist in multiple varieties ; most are of what is dubbed the " Closed Wreath " variety . Approximately five of the 1849 @-@ C Open Wreath are known ; one , believed the finest surviving specimen , sold at auction for $ 690 @,@ 000 in 2004 , remaining a record for the gold dollar series as of 2013 . One of the changes made during production was the inclusion of Longacre 's initial " L " on the truncation of Liberty 's neck , the first time a U.S. coin intended for full @-@ scale production had borne the initial of its designer . All issues beginning in 1850 bear the Closed Wreath . Beginning in 1854 , the gold dollar was also struck at the new San Francisco Mint .
| [
29401,
52663,
56437,
22590,
38499,
30989,
51514,
32462,
56942,
4712,
20394,
290,
279,
3491,
669,
294,
29299,
24415,
274,
116,
38250,
39141,
39802,
52028,
32227,
22590,
38499,
32462,
47437,
4712,
20394,
291,
281,
300,
21674,
38078,
4596,
39365,
59354,
32462,
47437,
4712,
22590,
38499,
21509,
279,
37678,
32487,
37598,
284,
299,
45,
65,
3473,
49,
21700,
63338,
281,
37451,
21286,
30869,
38961,
60727,
4706,
22590,
3491,
669,
30989,
45774,
30917,
64211,
279,
31351,
4423,
29299,
24415,
59392,
4811,
30859,
299,
46,
65,
32317,
22590,
45717,
281,
29401,
41825,
30635,
32462,
31983,
4450,
29299,
24415,
274,
116,
19827,
8570,
7856,
61345,
4424,
22590,
64211,
29401,
4811,
22590,
45348,
31432,
116,
4424,
58736,
279,
28732,
8366,
1891,
275,
4596,
50273,
276,
279,
21265,
20512,
50507,
294,
38078,
47437,
4424,
22590,
55651,
57104,
32074,
4706,
22590,
40050,
46338,
30917,
64211,
279,
59478,
4712,
32465,
22590,
30635,
32462,
56942,
281,
4089,
22590,
38078,
47437,
4424,
22590,
45348,
31432,
116,
4596,
3491,
669,
279,
31581,
46817,
47437,
4424,
58736,
275,
3491,
669,
299,
46,
65,
302,
276,
38427,
4596,
56679,
60727,
294,
31461,
21286,
4706,
32464,
4600,
45801,
22590,
269,
44130,
4335,
7397,
105,
269,
53264,
281,
64787,
30869,
4706,
22590,
3491,
669,
299,
46,
65,
302,
29513,
4335,
7397,
105,
21286,
38848,
294,
22226,
279,
55616,
22590,
45991,
60605,
57272,
279,
32069,
4424,
50978,
21700,
271,
3542,
49,
299,
45,
65,
3473,
49,
4596,
3493,
624,
279,
60376,
332,
47024,
21700,
22590,
30989,
45774,
47234,
4423,
4706,
3493,
633,
281,
20556,
4706,
22590,
51165,
31351,
45805,
62382,
22748,
22590,
59842,
4706,
29299,
24415,
274,
116,
52013,
269,
311,
269,
4712,
22590,
40026,
33944,
4706,
50395,
274,
116,
31505,
279,
22590,
38499,
32251,
332,
320,
47,
84,
47,
30474,
56474,
21700,
30923,
299,
46,
65,
39590,
62382,
21795,
37890,
22590,
52013,
4706,
21902,
55967,
281,
19407,
46340,
59220,
4596,
3491,
670,
30255,
22590,
44130,
4335,
7397,
105,
281,
58701,
4596,
3491,
674,
279,
22590,
30989,
45774,
22748,
30135,
47437,
4424,
22590,
22168,
20852,
58827,
29401,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The continued flow of gold from California made silver expensive in terms of gold , and U.S. silver coins began to flow out of the country for melting in 1849 , a flow that accelerated over the next several years as the price of the metal continued to rise . By 1853 , a thousand dollars in silver coin contained $ 1 @,@ 042 worth of bullion . As silver coins vanished , the gold dollar became the only federal coin in circulation between the cent and the quarter eagle ( $ 2 @.@ 50 piece ) . As such , it was struck in large numbers and widely circulated . According to Bowers in his book on the denomination , " the years 1850 to 1853 were the high @-@ water mark of the gold dollar , the glory years of the denomination when the little gold coins took the place of half dollars and silver dollars in everyday transactions . " This time came to an end in 1853 when Congress passed an act reducing the weight of most silver coins , allowing new issues of them to circulate .
| [
20996,
59392,
30881,
4706,
30989,
30917,
61312,
31351,
47282,
59682,
4596,
39920,
4706,
30989,
279,
21265,
320,
47,
84,
47,
47282,
38078,
37828,
4811,
30881,
22249,
4706,
22590,
51337,
21700,
52213,
4596,
3491,
669,
279,
332,
30881,
32227,
63246,
31601,
22590,
31515,
52869,
40237,
4423,
22590,
39349,
4706,
22590,
39013,
59392,
4811,
31886,
281,
3681,
3491,
673,
279,
332,
57423,
51514,
4596,
47282,
30474,
59385,
271,
284,
299,
45,
65,
3477,
51,
40218,
4706,
30349,
7874,
281,
3641,
47282,
38078,
57517,
279,
22590,
30989,
45774,
45283,
22590,
31581,
51726,
30474,
4596,
63338,
51035,
22590,
30424,
21265,
22590,
52624,
38327,
275,
271,
285,
299,
47,
65,
3523,
39278,
276,
281,
3641,
32139,
279,
4601,
22748,
47437,
4596,
38864,
52333,
21265,
47792,
61677,
281,
58657,
4811,
19538,
7500,
4596,
21823,
30314,
4712,
22590,
51427,
33944,
279,
269,
22590,
40237,
3491,
670,
4811,
3491,
673,
32462,
22590,
31082,
299,
46,
65,
40168,
31376,
4706,
22590,
30989,
45774,
279,
22590,
38600,
40237,
4706,
22590,
51427,
33944,
32465,
22590,
46454,
30989,
38078,
32272,
22590,
39291,
4706,
31040,
51514,
21265,
47282,
51514,
4596,
56155,
64595,
281,
269,
29894,
32251,
30383,
4811,
4419,
21616,
4596,
3491,
673,
32465,
54936,
46769,
4419,
21226,
57050,
22590,
47779,
4706,
31461,
47282,
38078,
279,
55492,
22168,
46340,
4706,
32229,
4811,
45476,
7066,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
As early as 1851 , New York Congressman William Duer alleged that that Patterson had made the gold dollar too small in diameter on purpose to provoke criticism . Patterson retired that year after 16 years in his position , and under his successor , George N. Eckert , annular gold dollar and half dollar patterns were struck . Public Ledger reported that although gold dollars would not be struck in annular form , gold half dollars would be , to help fill the need for change . With the new Pierce administration , Thomas M. Pettit took office as Mint Director on March 31 , 1853 . In April , Treasury Secretary James Guthrie wrote to Pettit that there were complaints that the gold dollar was too small , often lost or mistaken for a small silver coin , and enquiring about reports the Mint had experimented with annular dollars . Pettit replied , stating that none had been preserved , but enclosed a silver piece of equivalent size . He noted that while there would be technical difficulties in the production of the annular dollar , these could be overcome . In a letter dated May 10 , Pettit proposed an oval @-@ shaped holed piece , or an angular @-@ shaped coin , which would lessen the production problems . Pettit died suddenly on May 31 ; Guthrie did not let the issue fall , but queried Pettit 's replacement , James Ross Snowden , concerning the issue on June 7 . As U.S. coins were required to bear some device emblematic of liberty , the secretary hoped that artists could be found who could find some such design for an annular coin .
| [
3641,
38328,
4423,
3491,
671,
279,
20512,
30074,
63144,
50817,
19780,
115,
50883,
32227,
32227,
58938,
21795,
31351,
22590,
30989,
45774,
22614,
39720,
4596,
55989,
4712,
52610,
4811,
31770,
8335,
59425,
281,
58938,
52741,
32227,
32512,
37634,
3489,
40237,
4596,
21823,
56893,
279,
21265,
40062,
21823,
60588,
279,
44337,
313,
47,
19812,
7501,
279,
21268,
27265,
30989,
45774,
21265,
31040,
45774,
56832,
32462,
47437,
281,
44738,
20272,
7619,
57097,
32227,
55495,
30989,
51514,
40219,
22187,
4435,
47437,
4596,
21268,
27265,
30899,
279,
30989,
31040,
51514,
40219,
4435,
279,
4811,
31073,
30854,
22590,
31506,
21700,
45450,
281,
30050,
22590,
22168,
44704,
65107,
279,
44973,
312,
47,
20642,
8818,
32272,
46701,
4423,
29401,
54977,
4712,
36988,
3504,
279,
3491,
673,
281,
3913,
36295,
279,
55385,
58986,
36851,
19993,
1930,
1941,
40230,
4811,
20642,
8818,
32227,
39934,
32462,
61715,
32227,
22590,
30989,
45774,
22748,
22614,
39720,
279,
39171,
31334,
4715,
56651,
21700,
332,
39720,
47282,
30474,
279,
21265,
30761,
34829,
37598,
52720,
22590,
29401,
21795,
61980,
1843,
32487,
21268,
27265,
51514,
281,
20642,
8818,
52718,
279,
53001,
32227,
31529,
21795,
30259,
60240,
279,
21400,
56110,
332,
47282,
39278,
4706,
61952,
32031,
281,
3878,
39140,
32227,
40187,
39934,
40219,
4435,
60623,
64356,
4596,
22590,
62382,
4706,
22590,
21268,
27265,
45774,
279,
39936,
38128,
4435,
56791,
281,
3913,
332,
46432,
38192,
20394,
3483,
279,
20642,
8818,
56966,
4419,
31599,
299,
46,
65,
47252,
31098,
101,
39278,
279,
4715,
4419,
50913,
299,
46,
65,
47252,
30474,
279,
40186,
40219,
31277,
1853,
22590,
62382,
56939,
281,
20642,
8818,
30634,
57342,
4712,
20394,
3504,
294,
19993,
1930,
1941,
21532,
22187,
22001,
22590,
38809,
30815,
279,
21400,
31805,
7779,
20642,
8818,
274,
116,
63839,
279,
36851,
29697,
50680,
279,
61732,
22590,
38809,
4712,
29179,
290,
281,
3641,
320,
47,
84,
47,
38078,
32462,
57101,
4811,
30255,
32074,
45730,
45844,
24752,
4706,
52133,
279,
22590,
60465,
38709,
32227,
50961,
38128,
4435,
38547,
22762,
38128,
30858,
32074,
32139,
45717,
21700,
4419,
21268,
27265,
30474,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The Act of February 21 , 1853 , that had lightened the silver coins also authorized a gold three @-@ dollar piece , which began to be produced in 1854 . To ensure that the three @-@ dollar piece was not mistaken for other gold coins , it had been made thinner and wider than it would normally be , and Longacre put a distinctive design with an Indian princess on it . Longacre adapted both the technique and the design for the gold dollar , which was made thinner , and thus wider . An adaptation of Longacre 's princess for the larger gold coin was placed on the dollar , and a similar agricultural wreath on the reverse . The idea of making the gold dollar larger in this way had been suggested in Congress as early as 1852 , and had been advocated by Pettit , but Guthrie 's desire for an annular coin stalled the matter . In May 1854 , Snowden sent Guthrie a letter stating that the difficulties with an annular coin , especially in getting the coins to eject properly from the press , were more than trivial .
| [
20996,
19382,
4706,
55034,
3494,
279,
3491,
673,
279,
32227,
21795,
38895,
25260,
22590,
47282,
38078,
30135,
61620,
332,
30989,
39946,
299,
46,
65,
45774,
39278,
279,
40186,
37828,
4811,
4435,
56942,
4596,
3491,
674,
281,
4255,
45868,
32227,
22590,
39946,
299,
46,
65,
45774,
39278,
22748,
22187,
56651,
21700,
39193,
30989,
38078,
279,
4601,
21795,
30259,
31351,
53136,
21265,
40192,
32226,
4601,
40219,
56714,
4435,
279,
21265,
29299,
24415,
22339,
332,
63492,
45717,
32487,
4419,
44422,
56929,
4712,
4601,
281,
29299,
24415,
50853,
30322,
22590,
60624,
21265,
22590,
45717,
21700,
22590,
30989,
45774,
279,
40186,
22748,
31351,
53136,
279,
21265,
32239,
40192,
281,
3637,
61534,
4706,
29299,
24415,
274,
116,
56929,
21700,
22590,
46397,
30989,
30474,
22748,
46827,
4712,
22590,
45774,
279,
21265,
332,
52906,
64246,
22782,
7067,
4712,
22590,
52748,
281,
20996,
31135,
4706,
46500,
22590,
30989,
45774,
46397,
4596,
32234,
22752,
21795,
30259,
60590,
4596,
54936,
4423,
38328,
4423,
3491,
672,
279,
21265,
21795,
30259,
59098,
4450,
20642,
8818,
279,
21400,
19993,
1930,
1941,
274,
116,
45718,
21700,
4419,
21268,
27265,
30474,
52994,
22590,
46530,
281,
3913,
20394,
3491,
674,
279,
50680,
31983,
19993,
1930,
1941,
332,
46432,
53001,
32227,
22590,
64356,
32487,
4419,
21268,
27265,
30474,
279,
61953,
4596,
51844,
22590,
38078,
4811,
38344,
56962,
30917,
22590,
39347,
279,
32462,
31458,
32226,
53199,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Nevertheless , the Type 2 gold dollar ( as it came to be known ) proved unsatisfactory as the mints had difficulty in striking the new coin so that all details were brought out . This was due to the high relief of the design β the three Southern branch mints especially had trouble with the piece . Many of the Type 2 pieces quickly became illegible , and were sent back to Philadelphia for melting and recoinage . On most surviving specimens , the " 85 " in the date is not fully detailed . The Type 2 gold dollar was struck only at Philadelphia in 1854 and 1855 , at the three Southern branch mints in the latter year , and at San Francisco in 1856 , after the design was designated for replacement . To correct the problems , Longacre enlarged the head of Liberty , making it a scaled @-@ down version of the three @-@ dollar piece , and moved the lettering on the obverse closer to the rim . This improved the metal flow and design sharpness so much that early numismatic scholars assumed the reverse was also altered , though in fact no change was made and the Type 2 and Type 3 reverses are identical .
| [
64201,
279,
22590,
29937,
285,
30989,
45774,
275,
4423,
4601,
30383,
4811,
4435,
38848,
276,
46936,
22666,
33945,
40909,
4423,
22590,
31432,
116,
21795,
61865,
4596,
57323,
22590,
22168,
30474,
4788,
32227,
21256,
51454,
32462,
51097,
22249,
281,
29894,
22748,
21572,
4811,
22590,
31082,
47055,
4706,
22590,
45717,
22898,
22590,
39946,
55333,
45348,
31432,
116,
61953,
21795,
53200,
32487,
22590,
39278,
281,
29344,
4706,
22590,
29937,
285,
46817,
52628,
45283,
38742,
25656,
279,
21265,
32462,
31983,
30218,
4811,
64211,
21700,
52213,
21265,
31841,
7851,
1895,
281,
4095,
31461,
60605,
60536,
279,
22590,
269,
3558,
269,
4596,
22590,
30580,
4600,
22187,
38566,
55975,
281,
20996,
29937,
285,
30989,
45774,
22748,
47437,
31581,
4424,
64211,
4596,
3491,
674,
21265,
3491,
675,
279,
4424,
22590,
39946,
55333,
45348,
31432,
116,
4596,
22590,
46405,
32512,
279,
21265,
4424,
20852,
58827,
4596,
3491,
676,
279,
37634,
22590,
45717,
22748,
61848,
21700,
63839,
281,
4255,
51328,
22590,
56939,
279,
29299,
24415,
56123,
22590,
31060,
4706,
50395,
279,
46500,
4601,
332,
47180,
299,
46,
65,
30678,
53275,
4706,
22590,
39946,
299,
46,
65,
45774,
39278,
279,
21265,
39071,
22590,
46432,
7856,
4712,
22590,
4703,
35968,
45501,
4811,
22590,
22390,
281,
29894,
56418,
22590,
39013,
30881,
21265,
45717,
39657,
26307,
4788,
31466,
32227,
38328,
22196,
25956,
8807,
57166,
50970,
22590,
52748,
22748,
30135,
50890,
279,
47544,
4596,
30808,
4692,
45450,
22748,
31351,
21265,
22590,
29937,
285,
21265,
29937,
286,
52748,
116,
21286,
59808,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Design of Type 2 and 3 dollars = = =
| [
296,
296,
296,
44207,
4706,
29937,
285,
21265,
286,
51514,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The Type 2 and 3 gold dollars depict Liberty as a Native American princess , with a fanciful feathered headdress not resembling any worn by any Indian tribe . This image is an inexact copy of the design Longacre had made for the three @-@ dollar piece , and is one of a number of versions of Liberty Longacre created based on the Venus Accroupie or Crouching Venus , a sculpture then on display in a Philadelphia museum . For the reverse , Longacre adapted the " agricultural wreath " he had created for the reverse of the three @-@ dollar piece , composed of cotton , corn , tobacco , and wheat , blending the produce of North and South . This wreath would appear , later in the 1850s , on the Flying Eagle cent .
| [
20996,
29937,
285,
21265,
286,
30989,
51514,
45706,
50395,
4423,
332,
44627,
54830,
56929,
279,
32487,
332,
30818,
25749,
51724,
1843,
31060,
7380,
2194,
22187,
62497,
21273,
32501,
4450,
21273,
44422,
40011,
281,
29894,
38744,
4600,
4419,
31153,
6909,
30500,
4706,
22590,
45717,
29299,
24415,
21795,
31351,
21700,
22590,
39946,
299,
46,
65,
45774,
39278,
279,
21265,
4600,
22226,
4706,
332,
46685,
4706,
57527,
4706,
50395,
29299,
24415,
51351,
37810,
4712,
22590,
37530,
19379,
26950,
1941,
4715,
19665,
27220,
2065,
37530,
279,
332,
60462,
32230,
4712,
51497,
4596,
332,
64211,
46624,
281,
19907,
22590,
52748,
279,
29299,
24415,
50853,
22590,
269,
64246,
22782,
7067,
269,
4569,
21795,
51351,
21700,
22590,
52748,
4706,
22590,
39946,
299,
46,
65,
45774,
39278,
279,
55802,
4706,
45598,
279,
30503,
279,
53149,
279,
21265,
40183,
279,
55634,
22590,
52573,
4706,
37094,
21265,
37371,
281,
29894,
22782,
7067,
40219,
45185,
279,
38869,
4596,
22590,
3491,
670,
116,
279,
4712,
22590,
44301,
36606,
30424,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Art historian Cornelius Vermeule deprecated the Indian princess design used by Longacre for the obverses of the Types 2 and 3 gold dollar , and for the three @-@ dollar piece , " the ' princess ' of the gold coins is a banknote engraver 's elegant version of folk art of the 1850s . The plumes or feathers are more like the crest of the Prince of Wales than anything that saw the Western frontiers , save perhaps on a music hall beauty . "
| [
19439,
59798,
28689,
34267,
29974,
1860,
2011,
61836,
22590,
44422,
56929,
45717,
32354,
4450,
29299,
24415,
21700,
22590,
4703,
35968,
116,
4706,
22590,
37504,
285,
21265,
286,
30989,
45774,
279,
21265,
21700,
22590,
39946,
299,
46,
65,
45774,
39278,
279,
269,
22590,
274,
56929,
274,
4706,
22590,
30989,
38078,
4600,
332,
30230,
26333,
38373,
9018,
274,
116,
51575,
53275,
4706,
30887,
21291,
4706,
22590,
3491,
670,
116,
281,
20996,
31707,
1858,
4715,
56213,
21286,
31458,
31296,
22590,
38145,
4706,
22590,
44734,
4706,
37546,
32226,
55521,
32227,
22439,
22590,
50811,
56289,
116,
279,
31946,
52448,
4712,
332,
39082,
31041,
45282,
281,
269,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = War years = =
| [
296,
296,
21138,
40237,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The gold dollar continued to be produced in the late 1850s , though mintages declined from the figures of two million or more each year between 1850 and 1854 . Only about 51 @,@ 000 gold dollars were produced in 1860 , with over two @-@ thirds of that figure at Philadelphia , just under a third at San Francisco , and 1 @,@ 566 at Dahlonega . Roughly a hundred are known of the last , creating one of the great rarities from Dahlonega in the series .
| [
20996,
30989,
45774,
59392,
4811,
4435,
56942,
4596,
22590,
31255,
3491,
670,
116,
279,
47544,
31432,
24455,
55928,
30917,
22590,
51739,
4706,
22638,
52232,
4715,
31458,
30719,
32512,
51035,
3491,
670,
21265,
3491,
674,
281,
29512,
37598,
3524,
299,
45,
65,
3473,
49,
30989,
51514,
32462,
56942,
4596,
3491,
680,
279,
32487,
31601,
22638,
299,
46,
65,
39943,
116,
4706,
32227,
45980,
4424,
64211,
279,
31198,
40062,
332,
39943,
4424,
20852,
58827,
279,
21265,
284,
299,
45,
65,
3529,
55,
4424,
28732,
8366,
1891,
281,
37278,
2030,
332,
51949,
21286,
38848,
4706,
22590,
31254,
279,
55882,
22226,
4706,
22590,
38629,
4753,
8620,
7789,
30917,
28732,
8366,
1891,
4596,
22590,
47234,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The other candidate for the rarest from that mint is the 1861 @-@ D , with an estimated mintage of 1 @,@ 000 and perhaps 45 to 60 known . Two pairs of dies were shipped from Philadelphia to Dahlonega on December 10 , 1860 ; they arrived on January 7 , 1861 , two weeks before Georgia voted to secede from the Union , as the American Civil War began . Under orders from Governor Joseph E. Brown , state militia secured the mint , and at some point , small quantities of dollars and half eagles were produced . Records of how many coins were struck and when have not survived . Since dies crack in time , and all the mints were supplied with them from Philadelphia , coining could not last , and in May 1861 , coins and supplies remaining at Dahlonega were turned over to the treasury of the Confederate States of America , which Georgia had by then joined . Gold coins with a face value of $ 6 were put aside for assay . Normally , they would have been sent to Philadelphia to await the following year 's meeting of the United States Assay Commission , when they would be available for testing . Instead , these were sent to the initial Confederate capital of Montgomery , Alabama , though what was done with them there , and their ultimate fate , are unknown . The rarity of the 1861 @-@ D dollar , and the association with the Confederacy , make it especially prized .
| [
20996,
39193,
59255,
21700,
22590,
31828,
2195,
30917,
32227,
31432,
4600,
22590,
3491,
681,
299,
46,
65,
303,
279,
32487,
4419,
59646,
31432,
6935,
4706,
284,
299,
45,
65,
3473,
49,
21265,
52448,
3518,
4811,
3533,
38848,
281,
21042,
39218,
4706,
30635,
32462,
52884,
30917,
64211,
4811,
28732,
8366,
1891,
4712,
54965,
3483,
279,
3491,
680,
294,
32232,
50955,
4712,
50357,
290,
279,
3491,
681,
279,
22638,
40175,
45285,
50273,
40142,
4811,
22447,
7413,
30917,
22590,
37510,
279,
4423,
22590,
54830,
36484,
21138,
37828,
281,
37509,
46718,
30917,
55061,
44457,
304,
47,
36406,
279,
39802,
52230,
52832,
22590,
31432,
279,
21265,
4424,
32074,
39310,
279,
39720,
62426,
4706,
51514,
21265,
31040,
38327,
116,
32462,
56942,
281,
50606,
4706,
21835,
31370,
38078,
32462,
47437,
21265,
32465,
31059,
22187,
57365,
281,
37354,
30635,
38134,
4596,
32251,
279,
21265,
21256,
22590,
31432,
116,
32462,
57351,
32487,
32229,
30917,
64211,
279,
30474,
7856,
38128,
22187,
31254,
279,
21265,
4596,
20394,
3491,
681,
279,
38078,
21265,
57353,
60376,
4424,
28732,
8366,
1891,
32462,
47638,
31601,
4811,
22590,
22623,
33923,
4706,
22590,
63143,
44910,
4706,
49956,
279,
40186,
50273,
21795,
4450,
32230,
46350,
281,
28976,
38078,
32487,
332,
30807,
40093,
4706,
271,
289,
32462,
22339,
37755,
21700,
37758,
281,
55198,
279,
32232,
40219,
31059,
30259,
31983,
4811,
64211,
4811,
37790,
22590,
59725,
32512,
274,
116,
52211,
4706,
22590,
45010,
44910,
19444,
1757,
61321,
279,
32465,
32232,
40219,
4435,
59206,
21700,
53119,
281,
50342,
279,
39936,
32462,
31983,
4811,
22590,
52013,
63143,
51128,
4706,
61424,
279,
49945,
279,
47544,
32464,
22748,
30666,
32487,
32229,
39934,
279,
21265,
39931,
57481,
30827,
279,
21286,
53235,
281,
20996,
4753,
8620,
122,
4706,
22590,
3491,
681,
299,
46,
65,
303,
45774,
279,
21265,
22590,
63301,
32487,
22590,
54934,
6910,
279,
31358,
4601,
61953,
39358,
101,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Dahlonega , like the other two branch mints in the South , closed its doors after the 1861 strikings . It and the Charlotte facility never reopened ; the New Orleans Mint again struck coins from 1879 to 1909 , but did not strike gold dollars again . After 1861 , the only issuance of gold dollars outside Philadelphia was at San Francisco , in 1870 .
| [
28732,
8366,
1891,
279,
31296,
22590,
39193,
22638,
45348,
31432,
116,
4596,
22590,
37371,
279,
45500,
21902,
38286,
37634,
22590,
3491,
681,
57323,
116,
281,
3918,
21265,
22590,
58736,
56198,
39115,
47071,
1843,
294,
22590,
20512,
50507,
29401,
37635,
47437,
38078,
30917,
3491,
699,
4811,
3492,
629,
279,
21400,
21532,
22187,
47428,
30989,
51514,
37635,
281,
36250,
3491,
681,
279,
22590,
31581,
56504,
4706,
30989,
51514,
52391,
64211,
22748,
4424,
20852,
58827,
279,
4596,
3491,
690,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The outbreak of the Civil War shook public confidence in the Union , and citizens began hoarding specie , gold and silver coins . In late December 1861 , banks and then the federal Treasury stopped paying out gold at face value . By mid @-@ 1862 , all federal coins , even the base metal cent , had vanished from commerce in much of the country . The exception was the Far West , where for the most part , only gold and silver were acceptable currencies , and paper money traded at a discount . In the rest of the nation , gold and silver coins could be purchased from banks , exchange agents , and from the Treasury for a premium in the new greenbacks the government began to issue to fill the gap in commerce and finance the war .
| [
20996,
56781,
4706,
22590,
36484,
21138,
39671,
46946,
61744,
4596,
22590,
37510,
279,
21265,
55748,
37828,
4573,
41012,
32094,
1941,
279,
30989,
21265,
47282,
38078,
281,
3913,
31255,
54965,
3491,
681,
279,
37808,
21265,
32230,
22590,
51726,
55385,
53017,
46778,
22249,
30989,
4424,
30807,
40093,
281,
3681,
22089,
299,
46,
65,
3491,
682,
279,
21256,
51726,
38078,
279,
30788,
22590,
30243,
39013,
30424,
279,
21795,
57517,
30917,
55790,
4596,
31466,
4706,
22590,
51337,
281,
20996,
59661,
22748,
22590,
19878,
30030,
279,
40185,
21700,
22590,
31461,
31633,
279,
31581,
30989,
21265,
47282,
32462,
61517,
61809,
279,
21265,
39227,
39052,
47595,
4424,
332,
56009,
281,
3913,
22590,
31871,
4706,
22590,
46640,
279,
30989,
21265,
47282,
38078,
38128,
4435,
60302,
30917,
37808,
279,
56164,
45124,
279,
21265,
30917,
22590,
55385,
21700,
332,
52540,
4596,
22590,
22168,
38631,
34006,
22590,
62041,
37828,
4811,
38809,
4811,
30854,
22590,
21732,
4596,
55790,
21265,
51745,
22590,
22747,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Final years , abolition , and collecting = =
| [
296,
296,
36681,
40237,
279,
59055,
279,
21265,
61688,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
Since gold did not circulate in the United States ( except on the West Coast ) in the postwar period , much of the production of coins of that metal in the United States was double eagles for export . Accordingly , although 1 @,@ 361 @,@ 355 gold dollars were struck in 1862 β the last time production would exceed a million β the mintage fell to 6 @,@ 200 in 1863 and remained low for the rest of the coin 's existence , excepting 1873 and 1874 . The Mint felt it improper to suspend coinage of a coin authorized by Congress , and issued proof coins ( generally a few dozen to the tiny numismatic community ) from specially @-@ polished dies , also producing enough circulation strikes so that the proof coins would not be unduly rare . In 1873 and 1874 , old and worn gold dollars held by the government were melted and recoined , generating large mintages of that denomination . This was done in anticipation of the resumption of specie payments , which did not occur until the end of 1878 . Once specie again circulated at face value , the gold dollar found no place in commerce amid large quantities of silver coinage , either released from hoarding or newly struck by the Mint . The government expected that the resumption of specie payments would cause the dollar and other small gold coins to circulate again , but the public , allowed to redeem paper currency , continued to use it as more convenient than coins .
| [
37354,
30989,
21532,
22187,
45476,
7066,
4596,
22590,
45010,
44910,
275,
45913,
4712,
22590,
30030,
36504,
276,
4596,
22590,
31734,
9059,
46790,
279,
31466,
4706,
22590,
62382,
4706,
38078,
4706,
32227,
39013,
4596,
22590,
45010,
44910,
22748,
45786,
38327,
116,
21700,
45935,
281,
63125,
279,
55495,
284,
299,
45,
65,
3509,
50,
299,
45,
65,
3508,
54,
30989,
51514,
32462,
47437,
4596,
3491,
682,
22898,
22590,
31254,
32251,
62382,
40219,
45911,
332,
52232,
22898,
22590,
31432,
6935,
30839,
4811,
289,
299,
45,
65,
3493,
49,
4596,
3491,
683,
21265,
57080,
22034,
21700,
22590,
31871,
4706,
22590,
30474,
274,
116,
59677,
279,
45913,
7856,
3491,
693,
21265,
3491,
694,
281,
20996,
29401,
30840,
4601,
56417,
4811,
53077,
30474,
6935,
4706,
332,
30474,
61620,
4450,
54936,
279,
21265,
46338,
39365,
38078,
275,
59758,
332,
21674,
38292,
4811,
22590,
32254,
22196,
25956,
8807,
59324,
276,
30917,
60531,
299,
46,
65,
56884,
30635,
279,
30135,
60264,
45865,
63338,
53030,
4788,
32227,
22590,
39365,
38078,
40219,
22187,
4435,
22657,
8921,
31828,
281,
3913,
3491,
693,
21265,
3491,
694,
279,
22221,
21265,
32501,
30989,
51514,
31070,
4450,
22590,
62041,
32462,
46540,
21265,
31841,
25847,
279,
62034,
38864,
31432,
24455,
4706,
32227,
51427,
33944,
281,
29894,
22748,
30666,
4596,
64249,
4706,
22590,
22377,
49798,
4706,
32094,
1941,
56834,
279,
40186,
21532,
22187,
39166,
40076,
22590,
21616,
4706,
3491,
698,
281,
29511,
32094,
1941,
37635,
61677,
4424,
30807,
40093,
279,
22590,
30989,
45774,
38547,
4692,
39291,
4596,
55790,
30143,
38864,
62426,
4706,
47282,
30474,
6935,
279,
45833,
57072,
30917,
4573,
41012,
4715,
39117,
47437,
4450,
22590,
29401,
281,
20996,
62041,
56175,
32227,
22590,
22377,
49798,
4706,
32094,
1941,
56834,
40219,
37979,
22590,
45774,
21265,
39193,
39720,
30989,
38078,
4811,
45476,
7066,
37635,
279,
21400,
22590,
46946,
279,
50887,
4811,
47028,
39227,
55902,
279,
59392,
4811,
22681,
4601,
4423,
31458,
61784,
32226,
38078,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
In the 1870s and 1880s , public interest grew in the low @-@ mintage gold dollar . Collecting coins was becoming more popular , and a number of numismatists put aside some gold dollars and hoped for increases in value . The Mint most likely channeled its production through some favored Philadelphia dealers , though proof coins could be purchased for $ 1 @.@ 25 at the cashier 's window at the Philadelphia facility . Banks charged a premium for circulation strikes . They were popular in the jewelry trade , mounted into various items . The coins were often exported to China or Japan , where such jewelry was made . The dollars were often damaged in the process ; the Mint refused to sell into this trade and did its best to hinder it . Nevertheless , Mint officials concluded that jewelers were successful at getting the majority of each issue . Proof mintages exceeded 1 @,@ 000 by 1884 , and remained above that mark for the remainder of the series , numbers likely inflated by agents of jewelers , willing to pay the Mint 's premium of $ .25 per coin . Another use for the gold dollar was as a holiday gift ; after its abolition the quarter eagle became a popular present .
| [
3913,
22590,
3491,
690,
116,
21265,
3491,
700,
116,
279,
46946,
56477,
31010,
4596,
22590,
22034,
299,
46,
65,
31432,
6935,
30989,
45774,
281,
50086,
7856,
38078,
22748,
55611,
31458,
52516,
279,
21265,
332,
46685,
4706,
22196,
25956,
8817,
2218,
22339,
37755,
32074,
30989,
51514,
21265,
38709,
21700,
59847,
4596,
40093,
281,
20996,
29401,
31461,
46439,
51166,
1843,
21902,
62382,
53140,
32074,
51722,
64211,
51391,
279,
47544,
39365,
38078,
38128,
4435,
60302,
21700,
271,
284,
299,
47,
65,
3498,
4424,
22590,
30406,
7788,
274,
116,
47797,
4424,
22590,
64211,
56198,
281,
36329,
51169,
332,
52540,
21700,
63338,
53030,
281,
29893,
32462,
52516,
4596,
22590,
52061,
39997,
279,
52270,
31162,
53265,
38810,
281,
20996,
38078,
32462,
39171,
56186,
4811,
36473,
4715,
36854,
279,
40185,
32139,
52061,
22748,
31351,
281,
20996,
51514,
32462,
39171,
51382,
4596,
22590,
52571,
294,
22590,
29401,
52678,
4811,
31979,
31162,
32234,
39997,
21265,
21532,
21902,
30273,
4811,
46201,
4601,
281,
64201,
279,
29401,
60092,
59350,
32227,
38819,
7500,
32462,
62603,
4424,
51844,
22590,
56573,
4706,
30719,
38809,
281,
37206,
31432,
24455,
56163,
284,
299,
45,
65,
3473,
49,
4450,
3491,
704,
279,
21265,
57080,
37599,
32227,
31376,
21700,
22590,
60375,
4706,
22590,
47234,
279,
52333,
46439,
56449,
4450,
45124,
4706,
38819,
7500,
279,
53350,
4811,
22269,
22590,
29401,
274,
116,
52540,
4706,
271,
281,
645,
22278,
30474,
281,
49964,
22681,
21700,
22590,
30989,
45774,
22748,
4423,
332,
51933,
30967,
294,
37634,
21902,
59055,
22590,
52624,
38327,
45283,
332,
52516,
52544,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
James Pollock , in his final report as Mint Director in 1873 , advocated limiting striking of gold dollars to depositors who specifically requested it . " The gold dollar is not a convenient coin , on account of its small size , and it suffers more proportionately from abrasion than larger coins . " His successors called for its abolition , with James P. Kimball , before he left office in 1889 , writing to Congress that except as jewelry , " little practical use has been found for this coin " . Later that year , the new director , Edward O. Leech , issued a report stating that the gold dollar " is too small for circulation , and ... [ is ] used almost exclusively for the purposes of ornament . The last year in which the gold dollar was struck was 1889 . Congress abolished the gold dollar , along with the three @-@ cent nickel and three @-@ dollar piece , by the Act of September 26 , 1890 .
| [
36851,
29598,
8294,
279,
4596,
21823,
38491,
47080,
4423,
29401,
54977,
4596,
3491,
693,
279,
59098,
56549,
57323,
4706,
30989,
51514,
4811,
51436,
8409,
22762,
64571,
60391,
4601,
281,
269,
20996,
30989,
45774,
4600,
22187,
332,
61784,
30474,
279,
4712,
50845,
4706,
21902,
39720,
32031,
279,
21265,
4601,
53055,
31458,
62405,
33928,
30917,
37600,
7874,
32226,
46397,
38078,
281,
269,
20048,
60588,
116,
45395,
21700,
21902,
59055,
279,
32487,
36851,
315,
47,
20198,
24834,
279,
45285,
4569,
31269,
46701,
4596,
3491,
709,
279,
53371,
4811,
54936,
32227,
45913,
4423,
52061,
279,
269,
46454,
60212,
22681,
21800,
30259,
38547,
21700,
32234,
30474,
269,
281,
36918,
32227,
32512,
279,
22590,
22168,
56004,
279,
44246,
314,
47,
20273,
1791,
279,
46338,
332,
47080,
53001,
32227,
22590,
30989,
45774,
269,
4600,
22614,
39720,
21700,
63338,
279,
21265,
19312,
326,
4600,
328,
32354,
45145,
63552,
21700,
22590,
56994,
4706,
56779,
281,
20996,
31254,
32512,
4596,
40186,
22590,
30989,
45774,
22748,
47437,
22748,
3491,
709,
281,
54936,
59054,
22590,
30989,
45774,
279,
37678,
32487,
22590,
39946,
299,
46,
65,
30424,
46666,
21265,
39946,
299,
46,
65,
45774,
39278,
279,
4450,
22590,
19382,
4706,
58988,
3499,
279,
3491,
710,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
A total of 19 @,@ 499 @,@ 337 gold dollars were coined , of which 18 @,@ 223 @,@ 438 were struck at Philadelphia , 1 @,@ 004 @,@ 000 at New Orleans , 109 @,@ 138 at Charlotte , 90 @,@ 232 at San Francisco and 72 @,@ 529 at Dahlonega . According to an advertisement in the February 1899 issue of The Numismatist , gold dollars brought $ 1 @.@ 80 each , still in demand as a birthday present and for jewelry . That journal in 1905 carried news of a customer depositing 100 gold dollars into a bank ; the teller , aware of the value , credited the account with $ 1 @.@ 60 per coin . In 1908 , a dealer offered $ 2 each for any quantity . As coin collecting became a widespread pastime in the early 20th century , gold dollars became a popular specialty , a status they retain . The 2014 edition of R.S. Yeoman 's A Guide Book of United States Coins rates the least expensive gold dollar in very fine condition ( VF @-@ 20 ) at $ 300 , a value given for each of the Type 1 Philadelphia issues from 1849 to 1853 . Those seeking one of each type will find the most expensive to be a specimen of the Type 2 , with the 1854 and 1855 estimated at $ 350 in that condition ; the other two types have dates valued at $ 300 in that grade .
| [
300,
39984,
4706,
3492,
299,
45,
65,
3522,
58,
299,
45,
65,
3506,
56,
30989,
51514,
32462,
45515,
279,
4706,
40186,
3491,
299,
45,
65,
3495,
52,
299,
45,
65,
3516,
57,
32462,
47437,
4424,
64211,
279,
284,
299,
45,
65,
3473,
53,
299,
45,
65,
3473,
49,
4424,
20512,
50507,
279,
3483,
58,
299,
45,
65,
3486,
57,
4424,
58736,
279,
3563,
299,
45,
65,
3496,
51,
4424,
20852,
58827,
21265,
3545,
299,
45,
65,
3525,
58,
4424,
28732,
8366,
1891,
281,
58657,
4811,
4419,
64825,
4596,
22590,
55034,
3491,
719,
38809,
4706,
20996,
20532,
25956,
8817,
117,
279,
30989,
51514,
51097,
271,
284,
299,
47,
65,
3553,
30719,
279,
39820,
4596,
45694,
4423,
332,
55630,
52544,
21265,
21700,
52061,
281,
29889,
52064,
4596,
3492,
625,
51139,
31514,
4706,
332,
55905,
51436,
7856,
3483,
49,
30989,
51514,
31162,
332,
30230,
294,
22590,
32213,
1857,
279,
37793,
4706,
22590,
40093,
279,
55888,
22590,
50845,
32487,
271,
284,
299,
47,
65,
3533,
22278,
30474,
281,
3913,
3492,
628,
279,
332,
45667,
52349,
271,
285,
30719,
21700,
21273,
57005,
281,
3641,
30474,
61688,
45283,
332,
62728,
31636,
7844,
4596,
22590,
38328,
3493,
2209,
51158,
279,
30989,
51514,
45283,
332,
52516,
60532,
279,
332,
47401,
32232,
47095,
281,
20996,
3493,
634,
51562,
4706,
317,
47,
84,
47,
4350,
26440,
274,
116,
300,
36763,
28523,
4706,
45010,
44910,
28665,
116,
39443,
22590,
38879,
59682,
30989,
45774,
4596,
32386,
30859,
59354,
275,
321,
71,
299,
46,
65,
3493,
276,
4424,
271,
3503,
49,
279,
332,
40093,
38594,
21700,
30719,
4706,
22590,
29937,
284,
64211,
46340,
30917,
3491,
669,
4811,
3491,
673,
281,
37458,
52834,
22226,
4706,
30719,
32324,
32475,
30858,
22590,
31461,
59682,
4811,
4435,
332,
57272,
4706,
22590,
29937,
285,
279,
32487,
22590,
3491,
674,
21265,
3491,
675,
59646,
4424,
271,
3508,
49,
4596,
32227,
59354,
294,
22590,
39193,
22638,
40050,
31059,
38193,
47699,
4424,
271,
3503,
49,
4596,
32227,
38615,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Commemorative gold dollars = =
| [
296,
296,
28671,
7456,
42138,
30989,
51514,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The gold dollar had a brief resurrection during the period of Early United States commemorative coins . Between 1903 and 1922 nine different issues were produced , with a total mintage of 99 @,@ 799 . These were minted for various public events , did not circulate , and none used Longacre 's design .
| [
20996,
30989,
45774,
21795,
332,
37909,
64559,
45805,
22590,
46790,
4706,
36607,
45010,
44910,
55787,
33948,
38078,
281,
50014,
3492,
623,
21265,
3492,
642,
31521,
59513,
46340,
32462,
56942,
279,
32487,
332,
39984,
31432,
6935,
4706,
3572,
299,
45,
65,
3552,
58,
281,
37453,
32462,
31432,
1843,
21700,
53265,
46946,
45909,
279,
21532,
22187,
45476,
7066,
279,
21265,
31529,
32354,
29299,
24415,
274,
116,
45717,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
[] | [] |
|
= Johnson β Corey β Chaykovsky reaction =
| [
296,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The Johnson β Corey β Chaykovsky reaction ( sometimes referred to as the Corey β Chaykovsky reaction or CCR ) is a chemical reaction used in organic chemistry for the synthesis of epoxides , aziridines , and cyclopropanes . It was discovered in 1961 by A. William Johnson and developed significantly by E. J. Corey and Michael Chaykovsky . The reaction involves addition of a sulfur ylide to a ketone , aldehyde , imine , or enone to produce the corresponding 3 @-@ membered ring . The reaction is diastereoselective favoring trans substitution in the product regardless of the initial stereochemistry . The synthesis of epoxides via this method serves as an important retrosynthetic alternative to the traditional epoxidation reactions of olefins .
| [
20996,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
275,
60523,
57053,
4811,
4423,
22590,
28687,
122,
22897,
19630,
2330,
35333,
57020,
4715,
3684,
83,
276,
4600,
332,
55732,
57020,
32354,
4596,
52378,
59288,
21700,
22590,
60615,
4706,
4518,
35344,
116,
279,
4430,
7897,
7356,
1858,
279,
21265,
38173,
26749,
24579,
281,
3918,
22748,
61885,
4596,
3492,
681,
4450,
300,
47,
50817,
50361,
21265,
59506,
65012,
4450,
304,
47,
309,
47,
28687,
122,
21265,
50441,
19630,
2330,
35333,
281,
20996,
57020,
56501,
55452,
4706,
332,
47462,
356,
8088,
102,
4811,
332,
21951,
8366,
279,
21251,
1847,
2326,
102,
279,
4595,
7854,
279,
4715,
4517,
8366,
4811,
52573,
22590,
64882,
286,
299,
46,
65,
46541,
1843,
31883,
281,
20996,
57020,
4600,
30627,
27131,
8415,
26114,
7938,
38458,
7856,
40002,
64581,
4596,
22590,
52574,
62461,
4706,
22590,
52013,
47406,
24988,
34872,
281,
20996,
60615,
4706,
4518,
35344,
116,
22705,
32234,
46561,
47237,
4423,
4419,
59829,
47101,
9132,
34560,
63277,
4811,
22590,
63933,
4518,
26634,
33944,
60318,
4706,
22222,
7566,
116,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The reaction is most often employed for epoxidation via methylene transfer , and to this end has been used in several notable total syntheses ( See Synthesis of epoxides below ) . Additionally detailed below are the history , mechanism , scope , and enantioselective variants of the reaction . Several reviews have been published .
| [
20996,
57020,
4600,
31461,
39171,
56104,
21700,
4518,
26634,
33944,
22705,
46562,
7464,
57455,
279,
21265,
4811,
32234,
21616,
21800,
30259,
32354,
4596,
52869,
52321,
39984,
53086,
1858,
275,
20869,
20945,
27147,
1955,
4706,
4518,
35344,
116,
37837,
276,
281,
64164,
55975,
37837,
21286,
22590,
51929,
279,
59994,
279,
39606,
279,
21265,
4517,
24613,
8415,
26114,
7938,
57520,
4706,
22590,
57020,
281,
50666,
52749,
31059,
30259,
60299,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = History = =
| [
296,
296,
50309,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The original publication by Johnson concerned the reaction of 9 @-@ dimethylsulfonium fluorenylide with substituted benzaldehyde derivatives . The attempted Wittig @-@ like reaction failed and a benzalfluorene oxide was obtained instead , noting that " Reaction between the sulfur ylid and benzaldehydes did not afford benzalfluorenes as had the phosphorus and arsenic ylids . "
| [
20996,
56778,
63815,
4450,
50361,
59349,
22590,
57020,
4706,
292,
299,
46,
65,
21537,
34410,
2196,
2012,
35220,
38526,
7476,
8088,
102,
32487,
63895,
30269,
53764,
63454,
281,
20996,
59189,
30051,
1943,
299,
46,
65,
31296,
57020,
45953,
21265,
332,
30269,
6980,
2026,
26523,
102,
39209,
22748,
56741,
52028,
279,
46680,
32227,
269,
55271,
51035,
22590,
47462,
356,
8088,
21265,
30269,
53764,
116,
21532,
22187,
45119,
30269,
6980,
2026,
26523,
1858,
4423,
21795,
22590,
46804,
26554,
21265,
37751,
1939,
356,
8088,
116,
281,
269,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The subsequent development of ( dimethyloxosulfaniumyl ) methanide , ( CH3 ) 2SOCH2 and ( dimethylsulfaniumyl ) methanide , ( CH3 ) 2SCH2 ( known as Corey β Chaykovsky reagents ) by Corey and Chaykovsky as efficient methylene @-@ transfer reagents established the reaction as a part of the organic canon .
| [
20996,
62597,
63469,
4706,
275,
21537,
34410,
2107,
2102,
8912,
33798,
2331,
276,
31417,
7009,
1818,
279,
275,
3689,
52,
276,
285,
6576,
73,
51,
21265,
275,
21537,
34410,
2196,
2012,
33798,
2331,
276,
31417,
7009,
1818,
279,
275,
3689,
52,
276,
285,
6554,
51,
275,
38848,
4423,
28687,
122,
22897,
19630,
2330,
35333,
4757,
40922,
276,
4450,
28687,
122,
21265,
19630,
2330,
35333,
4423,
59594,
46562,
7464,
299,
46,
65,
57455,
4757,
40922,
63542,
22590,
57020,
4423,
332,
31633,
4706,
22590,
52378,
37957,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Mechanism = =
| [
296,
296,
44569,
7915,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The reaction mechanism for the Johnson β Corey β Chaykovsky reaction consists of nucleophilic addition of the ylide to the carbonyl or imine group . A negative charge is transferred to the heteroatom and because the sulfonium cation is a good leaving group it gets expelled forming the ring . In the related Wittig reaction , the formation of the much stronger phosphorus @-@ oxygen double bond prevents oxirane formation and instead , olefination takes place through a 4 @-@ membered cyclic intermediate .
| [
20996,
57020,
59994,
21700,
22590,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
55833,
4706,
39146,
35231,
1939,
55452,
4706,
22590,
356,
8088,
102,
4811,
22590,
45415,
2331,
4715,
4595,
7854,
38640,
281,
300,
56703,
45453,
4600,
63937,
4811,
22590,
46194,
24760,
21265,
51018,
22590,
32149,
35220,
21417,
7874,
4600,
332,
30992,
52115,
38640,
4601,
30965,
56176,
51788,
22590,
31883,
281,
3913,
22590,
52693,
30051,
1943,
57020,
279,
22590,
59733,
4706,
22590,
31466,
57326,
46804,
26554,
299,
46,
65,
46739,
45786,
30312,
56925,
4721,
25916,
102,
59733,
21265,
52028,
279,
22222,
7566,
33944,
39888,
39291,
53140,
332,
287,
299,
46,
65,
46541,
1843,
45649,
64456,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The trans diastereoselectivity observed results from the reversibility of the initial addition , allowing equilibration to the favored anti betaine over the syn betaine . Initial addition of the ylide results in a betaine with adjacent charges ; density functional theory calculations have shown that the rate @-@ limiting step is rotation of the central bond into the conformer necessary for backside attack on the sulfonium .
| [
20996,
40002,
30627,
27131,
8415,
26114,
34925,
56734,
52738,
30917,
22590,
47106,
49224,
4706,
22590,
52013,
55452,
279,
55492,
51640,
42137,
4811,
22590,
51722,
30160,
30274,
7854,
31601,
22590,
22543,
30274,
7854,
281,
50339,
55452,
4706,
22590,
356,
8088,
102,
52738,
4596,
332,
30274,
7854,
32487,
55457,
51171,
294,
51431,
62030,
47535,
64268,
31059,
39679,
32227,
22590,
31830,
299,
46,
65,
56549,
32115,
4600,
57147,
4706,
22590,
51156,
30312,
31162,
22590,
51285,
1857,
60050,
21700,
37799,
7771,
45233,
4712,
22590,
32149,
35220,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The degree of reversibility in the initial step ( and therefore the diastereoselectivity ) depends on four factors , with greater reversibility corresponding to higher selectivity :
| [
20996,
45690,
4706,
47106,
49224,
4596,
22590,
52013,
32115,
275,
21265,
60645,
22590,
30627,
27131,
8415,
26114,
34925,
276,
51434,
4712,
30905,
51703,
279,
32487,
51867,
47106,
49224,
64882,
4811,
46198,
47219,
34925,
293,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Stability of the substrate with higher stability leading to greater reversibility by favoring the starting material over the betaine .
| [
20923,
7154,
7933,
4706,
22590,
60583,
32487,
46198,
60547,
52107,
4811,
51867,
47106,
49224,
4450,
38458,
7856,
22590,
57295,
56596,
31601,
22590,
30274,
7854,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Stability of the ylide with higher stability similarly leading to greater reversibility .
| [
20923,
7154,
7933,
4706,
22590,
356,
8088,
102,
32487,
46198,
60547,
60505,
52107,
4811,
51867,
47106,
49224,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Steric hindrance in the betaine with greater hindrance leading to greater reversibility by disfavoring formation of the intermediate and slowing the rate @-@ limiting rotation of the central bond .
| [
29825,
1939,
31086,
35492,
4596,
22590,
30274,
7854,
32487,
51867,
31086,
35492,
52107,
4811,
51867,
47106,
49224,
4450,
21542,
34440,
7856,
59733,
4706,
22590,
64456,
21265,
52931,
22590,
31830,
299,
46,
65,
56549,
57147,
4706,
22590,
51156,
30312,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Solvation of charges in the betaine by counterions such as lithium with greater solvation allowing more facile rotation in the betaine intermediate , lowering the amount of reversibility .
| [
20906,
42486,
4706,
51171,
4596,
22590,
30274,
7854,
4450,
51336,
25897,
32139,
4423,
52147,
32487,
51867,
22497,
42486,
55492,
31458,
45948,
57147,
4596,
22590,
30274,
7854,
64456,
279,
56566,
22590,
45157,
4706,
47106,
49224,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Scope = =
| [
296,
296,
20864,
2115,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The application of the Johnson β Corey β Chaykovsky reaction in organic synthesis is diverse . The reaction has come to encompass reactions of many types of sulfur ylides with electrophiles well beyond the original publications . It has seen use in a number of high @-@ profile total syntheses , as detailed below , and is generally recognized as a powerful transformative tool in the organic repertoire .
| [
20996,
63287,
4706,
22590,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
4596,
52378,
60615,
4600,
51507,
281,
20996,
57020,
21800,
30482,
4811,
59624,
60318,
4706,
31370,
40050,
4706,
47462,
356,
8088,
1858,
32487,
59601,
25783,
32458,
45302,
22590,
56778,
64538,
281,
3918,
21800,
31968,
22681,
4596,
332,
46685,
4706,
31082,
299,
46,
65,
52578,
39984,
53086,
1858,
279,
4423,
55975,
37837,
279,
21265,
4600,
59758,
62438,
4423,
332,
56900,
60666,
33948,
32273,
4596,
22590,
52378,
62483,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Types of ylides = = =
| [
296,
296,
296,
37504,
4706,
356,
8088,
1858,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
Many types of ylides can be prepared with various functional groups both on the anionic carbon center and on the sulfur . The substitution pattern can influence the ease of preparation for the reagents ( typically from the sulfonium halide , e.g. trimethylsulfonium iodide ) and overall reaction rate in various ways . The general format for the reagent is shown on the right .
| [
29344,
40050,
4706,
356,
8088,
1858,
21413,
4435,
56914,
32487,
53265,
62030,
46131,
30322,
4712,
22590,
4419,
34811,
45415,
45443,
21265,
4712,
22590,
47462,
281,
20996,
64581,
52427,
21413,
59859,
22590,
30722,
4706,
63781,
21700,
22590,
4757,
40922,
275,
60687,
30917,
22590,
32149,
35220,
21796,
7771,
279,
336,
47,
104,
47,
32306,
34410,
2196,
2012,
35220,
21890,
7771,
276,
21265,
52394,
57020,
31830,
4596,
53265,
32448,
281,
20996,
51832,
46028,
21700,
22590,
4757,
33665,
4600,
39679,
4712,
22590,
39523,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Use of a sulfoxonium allows more facile preparation of the reagent using weaker bases as compared to sulfonium ylides . ( The difference being that a sulfoxonium contains a doubly bonded oxygen whereas the sulfonium does not . ) The former react slower due to their increased stability . In addition , the dialkylsulfoxide by @-@ products of sulfoxonium reagents are greatly preferred to the significantly more toxic , volatile , and odorous dialkylsulfide by @-@ products from sulfonium reagents .
| [
21075,
4706,
332,
32149,
2107,
35220,
45143,
31458,
45948,
63781,
4706,
22590,
4757,
33665,
40085,
47773,
37811,
4423,
55794,
4811,
32149,
35220,
356,
8088,
1858,
281,
275,
20996,
61863,
37832,
32227,
332,
32149,
2107,
35220,
55842,
332,
45787,
45330,
46739,
53339,
22590,
32149,
35220,
30659,
22187,
281,
276,
20996,
46030,
39447,
47313,
21572,
4811,
39931,
59846,
60547,
281,
3913,
55452,
279,
22590,
30625,
2006,
2024,
8912,
35344,
4450,
299,
46,
65,
56945,
4706,
32149,
2107,
35220,
4757,
40922,
21286,
51868,
60227,
4811,
22590,
65012,
31458,
39992,
279,
57543,
279,
21265,
31571,
8439,
30625,
2006,
2024,
8912,
7771,
4450,
299,
46,
65,
56945,
30917,
32149,
35220,
4757,
40922,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The vast majority of reagents are monosubstituted at the ylide carbon ( either R1 or R2 as hydrogen ) . Disubstituted reagents are much rarer but have been described :
| [
20996,
32373,
56573,
4706,
4757,
40922,
21286,
31453,
35724,
7932,
8789,
4424,
22590,
356,
8088,
102,
45415,
275,
45833,
317,
50,
4715,
317,
51,
4423,
56392,
276,
281,
19753,
8864,
8818,
27382,
4757,
40922,
21286,
31466,
31828,
115,
21400,
31059,
30259,
59488,
293,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
If the ylide carbon is substituted with an electron @-@ withdrawing group ( EWG ) , the reagent is referred to as a stabilized ylide . These , similarly to sulfoxonium reagents , react much slower and are typically easier to prepare . These are limited in their usefulness as the reaction can become prohibitively sluggish : examples involving amides are widespread , with many fewer involving esters and virtually no examples involving other EWG 's . For these , the related Darzens reaction is typically more appropriate .
| [
3908,
22590,
356,
8088,
102,
45415,
4600,
63895,
32487,
4419,
56087,
299,
46,
65,
63982,
38640,
275,
3774,
72,
276,
279,
22590,
4757,
33665,
4600,
57053,
4811,
4423,
332,
62570,
356,
8088,
102,
281,
37453,
279,
60505,
4811,
32149,
2107,
35220,
4757,
40922,
279,
39447,
31466,
47313,
21265,
21286,
60687,
45819,
4811,
52543,
281,
37453,
21286,
52140,
4596,
39931,
62701,
4423,
22590,
57020,
21413,
45284,
56951,
34918,
32054,
7632,
105,
293,
56162,
59927,
30143,
1858,
21286,
62728,
279,
32487,
31370,
38475,
59927,
30780,
2168,
21265,
60741,
4692,
56162,
59927,
39193,
3774,
72,
274,
116,
281,
19907,
39936,
279,
22590,
52693,
19720,
27550,
57020,
4600,
60687,
31458,
63291,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
If the ylide carbon is substituted with an aryl or allyl group , the reagent is referred to as a semi @-@ stabilized ylide . These have been developed extensively , second only to the classical methylene reagents ( R1 = R2 = H ) . The substitution pattern on aryl reagents can heavily influence the selectivity of the reaction as per the criteria above .
| [
3908,
22590,
356,
8088,
102,
45415,
4600,
63895,
32487,
4419,
4422,
2331,
4715,
30134,
109,
38640,
279,
22590,
4757,
33665,
4600,
57053,
4811,
4423,
332,
31980,
299,
46,
65,
62570,
356,
8088,
102,
281,
37453,
31059,
30259,
59506,
63566,
279,
47205,
31581,
4811,
22590,
59296,
46562,
7464,
4757,
40922,
275,
317,
50,
296,
317,
51,
296,
307,
276,
281,
20996,
64581,
52427,
4712,
4422,
2331,
4757,
40922,
21413,
51919,
59859,
22590,
47219,
34925,
4706,
22590,
57020,
4423,
22278,
22590,
55891,
37599,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
If the ylide carbon is substituted with an alkyl group the reagent is referred to as an unstabilized ylide . The size of the alkyl groups are the major factors in selectivity with these reagents .
| [
3908,
22590,
356,
8088,
102,
45415,
4600,
63895,
32487,
4419,
37665,
38640,
22590,
4757,
33665,
4600,
57053,
4811,
4423,
4419,
22666,
8773,
7835,
9150,
356,
8088,
102,
281,
20996,
32031,
4706,
22590,
37665,
46131,
21286,
22590,
38961,
51703,
4596,
47219,
34925,
32487,
39936,
4757,
40922,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The R @-@ groups on the sulfur , though typically methyls , have been used to synthesize reagents that can perform enantioselective variants of the reaction ( See Variations below ) . The size of the groups can also influence diastereoselectivity in alicyclic substrates .
| [
20996,
317,
299,
46,
65,
46131,
4712,
22590,
47462,
279,
47544,
60687,
46562,
116,
279,
31059,
30259,
32354,
4811,
53086,
7946,
4757,
40922,
32227,
21413,
52446,
4517,
24613,
8415,
26114,
7938,
57520,
4706,
22590,
57020,
275,
20869,
29966,
41066,
37837,
276,
281,
20996,
32031,
4706,
22590,
46131,
21413,
30135,
59859,
30627,
27131,
8415,
26114,
34925,
4596,
21254,
25098,
1939,
62601,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Synthesis of epoxides = = =
| [
296,
296,
296,
20945,
27147,
1955,
4706,
4518,
35344,
116,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
Reactions of sulfur ylides with ketones and aldehydes to form epoxides are by far the most common application of the Johnson β Corey β Chaykovsky reaction . Examples involving complex substrates and ' exotic ' ylides have been reported , as shown below .
| [
55271,
116,
4706,
47462,
356,
8088,
1858,
32487,
21951,
26465,
21265,
21251,
1847,
2326,
1858,
4811,
30899,
4518,
35344,
116,
21286,
4450,
21660,
22590,
31461,
45534,
63287,
4706,
22590,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
281,
55018,
59927,
51258,
62601,
21265,
274,
45923,
274,
356,
8088,
1858,
31059,
30259,
57097,
279,
4423,
39679,
37837,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The reaction has been used in a number of notable total syntheses including the Danishefsky Taxol total synthesis , which produces the chemotherapeutic drug taxol , and the Kuehne Strychnine total synthesis which produces the pesticide strychnine .
| [
20996,
57020,
21800,
30259,
32354,
4596,
332,
46685,
4706,
52321,
39984,
53086,
1858,
59841,
22590,
44188,
1845,
8728,
20982,
2096,
39984,
60615,
279,
40186,
56944,
22590,
30436,
35297,
48867,
30686,
22572,
2096,
279,
21265,
22590,
3963,
1847,
2063,
20926,
9116,
26321,
39984,
60615,
40186,
56944,
22590,
60164,
22522,
9116,
26321,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Synthesis of aziridines = = =
| [
296,
296,
296,
20945,
27147,
1955,
4706,
4430,
7897,
7356,
1858,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The synthesis of aziridines from imines is another important application of the Johnson β Corey β Chaykovsky reaction and provides an alternative to amine transfer from oxaziridines . Though less widely applied , the reaction has a similar substrate scope and functional group tolerance to the carbonyl equivalent . The examples shown below are representative ; in the latter , an aziridine forms in situ and is opened via nucleophilic attack to form the corresponding amine .
| [
20996,
60615,
4706,
4430,
7897,
7356,
1858,
30917,
4595,
25853,
4600,
50919,
59829,
63287,
4706,
22590,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
21265,
56978,
4419,
63277,
4811,
30144,
102,
57455,
30917,
4721,
7105,
8607,
25853,
281,
44974,
31277,
47792,
50937,
279,
22590,
57020,
21800,
332,
52906,
60583,
39606,
21265,
62030,
38640,
60657,
4811,
22590,
45415,
2331,
61952,
281,
20996,
56162,
39679,
37837,
21286,
65162,
294,
4596,
22590,
46405,
279,
4419,
4430,
7897,
7356,
102,
38541,
4596,
32030,
21265,
4600,
46707,
22705,
39146,
35231,
1939,
45233,
4811,
30899,
22590,
64882,
30144,
102,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Synthesis of cyclopropanes = = =
| [
296,
296,
296,
20945,
27147,
1955,
4706,
38173,
26749,
24579,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
For addition of sulfur ylides to enones , higher 1 @,@ 4 @-@ selectivity is typically obtained with sulfoxonium reagents than with sulfonium reagents . Many electron @-@ withdrawing groups have been shown compatible with the reaction including ketones , esters , and amides ( the example below involves a Weinreb amide ) . With further conjugated systems 1 @,@ 6 @-@ addition tends to predominate over 1 @,@ 4 @-@ addition .
| [
19907,
55452,
4706,
47462,
356,
8088,
1858,
4811,
4517,
26465,
279,
46198,
284,
299,
45,
65,
287,
299,
46,
65,
47219,
34925,
4600,
60687,
56741,
32487,
32149,
2107,
35220,
4757,
40922,
32226,
32487,
32149,
35220,
4757,
40922,
281,
29344,
56087,
299,
46,
65,
63982,
46131,
31059,
30259,
39679,
61709,
32487,
22590,
57020,
59841,
21951,
26465,
279,
30780,
2168,
279,
21265,
30143,
1858,
275,
22590,
51668,
37837,
56501,
332,
30024,
8577,
30143,
102,
276,
281,
30050,
51816,
59366,
101,
53087,
284,
299,
45,
65,
289,
299,
46,
65,
55452,
39914,
4811,
56906,
7066,
31601,
284,
299,
45,
65,
287,
299,
46,
65,
55452,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Other reactions = = =
| [
296,
296,
296,
37121,
60318,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
In addition to the reactions originally reported by Johnson , Corey , and Chaykovsky , sulfur ylides have been used for a number of related homologation reactions that tend to be grouped under the same name .
| [
3913,
55452,
4811,
22590,
60318,
62275,
57097,
4450,
50361,
279,
28687,
122,
279,
21265,
19630,
2330,
35333,
279,
47462,
356,
8088,
1858,
31059,
30259,
32354,
21700,
332,
46685,
4706,
52693,
51935,
33944,
60318,
32227,
32216,
4811,
4435,
51874,
40062,
22590,
31937,
31496,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
With epoxides and aziridines the reaction serves as a ring @-@ expansion to produce the corresponding oxetane or azetidine . The long reaction times required for these reactions prevent them from occurring as significant side reactions when synthesizing epoxides and aziridines .
| [
30050,
4518,
35344,
116,
21265,
4430,
7897,
7356,
1858,
22590,
57020,
47237,
4423,
332,
31883,
299,
46,
65,
59679,
4811,
52573,
22590,
64882,
4721,
7515,
2063,
4715,
4430,
7519,
7356,
102,
281,
20996,
31323,
57020,
39962,
57101,
21700,
39936,
60318,
52551,
32229,
30917,
60088,
4423,
63870,
32011,
60318,
32465,
53086,
34932,
4518,
35344,
116,
21265,
4430,
7897,
7356,
1858,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Several cycloadditions wherein the ylide serves as a " nucleophilic carbenoid equivalent " have been reported .
| [
50666,
38173,
53756,
116,
53341,
22590,
356,
8088,
102,
47237,
4423,
332,
269,
39146,
35231,
1939,
30395,
7471,
1940,
61952,
269,
31059,
30259,
57097,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
Living polymerizations using trialkylboranes as the catalyst and ( dimethyloxosulfaniumyl ) methanide as the monomer have been reported for the synthesis of various complex polymers .
| [
44524,
52512,
54114,
40085,
40010,
2006,
2008,
26513,
1858,
4423,
22590,
55699,
21265,
275,
21537,
34410,
2107,
2102,
8912,
33798,
2331,
276,
31417,
7009,
1818,
4423,
22590,
31453,
8163,
31059,
30259,
57097,
21700,
22590,
60615,
4706,
53265,
51258,
56888,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = Enantioselective variations = =
| [
296,
296,
3785,
24613,
8415,
26114,
7938,
62705,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The development of an enantioselective ( i.e. yielding an enantiomeric excess , which is labelled as " ee " ) variant of the Johnson β Corey β Chaykovsky reaction remains an active area of academic research . The use of chiral sulfides in a stoichiometric fashion has proved more successful than the corresponding catalytic variants , but the substrate scope is still limited in all cases . The catalytic variants have been developed almost exclusively for enantioselective purposes ; typical organosulfide reagents are not prohibitively expensive and the racemic reactions can be carried out with equimolar amounts of ylide without raising costs significantly . Chiral sulfides , on the other hand , are more costly to prepare , spurring the advancement of catalytic enantioselective methods .
| [
20996,
63469,
4706,
4419,
4517,
24613,
8415,
26114,
7938,
275,
340,
47,
102,
47,
57581,
4419,
4517,
24613,
26446,
1939,
45914,
279,
40186,
4600,
56526,
4423,
269,
4508,
269,
276,
53263,
4706,
22590,
50361,
22897,
28687,
122,
22897,
19630,
2330,
35333,
57020,
52701,
4419,
45096,
30173,
4706,
55427,
57103,
281,
20996,
22681,
4706,
30443,
1744,
32149,
25703,
4596,
332,
22521,
25669,
49467,
51717,
21800,
46936,
31458,
62603,
32226,
22590,
64882,
59268,
57520,
279,
21400,
22590,
60583,
39606,
4600,
39820,
52140,
4596,
21256,
37970,
281,
20996,
59268,
57520,
31059,
30259,
59506,
45145,
63552,
21700,
4517,
24613,
8415,
26114,
7938,
56994,
294,
53216,
39191,
2102,
8912,
7771,
4757,
40922,
21286,
22187,
56951,
34918,
59682,
21265,
22590,
31813,
8169,
60318,
21413,
4435,
51139,
22249,
32487,
21625,
7848,
8058,
50897,
4706,
356,
8088,
102,
53356,
52636,
38124,
65012,
281,
19632,
8562,
32149,
25703,
279,
4712,
22590,
39193,
31044,
279,
21286,
31458,
45597,
4811,
52543,
279,
32103,
26901,
22590,
63265,
4706,
59268,
4517,
24613,
8415,
26114,
7938,
52224,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
= = = Stoichiometric reagents = = =
| [
296,
296,
296,
20925,
25669,
49467,
4757,
40922,
296,
296,
296,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
[] | [] |
|
The most successful reagents employed in a stoichiometric fashion are shown below . The first is a bicyclic oxathiane that has been employed in the synthesis of the Ξ² @-@ adrenergic compound dichloroisoproterenol ( DCI ) but is limited by the availability of only one enantiomer of the reagent . The synthesis of the axial diastereomer is rationalized via the 1 @,@ 3 @-@ anomeric effect which reduces the nucleophilicity of the equatorial lone pair . The conformation of the ylide is limited by transannular strain and approach of the aldehyde is limited to one face of the ylide by steric interactions with the methyl substituents .
| [
20996,
31461,
62603,
4757,
40922,
56104,
4596,
332,
22521,
25669,
49467,
51717,
21286,
39679,
37837,
281,
20996,
38499,
4600,
332,
30277,
25026,
4721,
24748,
7006,
32227,
21800,
30259,
56104,
4596,
22590,
60615,
4706,
22590,
5035,
299,
46,
65,
37627,
34364,
55804,
30629,
8114,
8332,
26507,
27131,
2073,
109,
275,
3723,
74,
276,
21400,
4600,
52140,
4450,
22590,
64264,
4706,
31581,
22226,
4517,
24613,
26446,
4706,
22590,
4757,
33665,
281,
20996,
60615,
4706,
22590,
37795,
30627,
27131,
26446,
4600,
57017,
26031,
22705,
22590,
284,
299,
45,
65,
286,
299,
46,
65,
30155,
25316,
45828,
40186,
52669,
22590,
39146,
35231,
34616,
4706,
22590,
21625,
48897,
31322,
31614,
281,
20996,
51285,
33944,
4706,
22590,
356,
8088,
102,
4600,
52140,
4450,
40002,
7012,
27265,
47418,
21265,
55532,
4706,
22590,
21251,
1847,
2326,
102,
4600,
52140,
4811,
22226,
30807,
4706,
22590,
356,
8088,
102,
4450,
32116,
1939,
64453,
32487,
22590,
46562,
53047,
27239,
116,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |
The other major reagent is a camphor @-@ derived reagent developed by Varinder Aggarwal of the University of Bristol . Both enantiomers are easily synthesized , although the yields are lower than for the oxathiane reagent . The ylide conformation is determined by interaction with the bridgehead hydrogens and approach of the aldehyde is blocked by the camphor moiety . The reaction employs a phosphazene base to promote formation of the ylide .
| [
20996,
39193,
38961,
4757,
33665,
4600,
332,
30384,
7712,
299,
46,
65,
51438,
4757,
33665,
59506,
4450,
29966,
26295,
19391,
1750,
9056,
4706,
22590,
61502,
4706,
50027,
281,
28530,
4517,
24613,
35200,
21286,
45820,
63914,
279,
55495,
22590,
47826,
21286,
38940,
32226,
21700,
22590,
4721,
24748,
7006,
4757,
33665,
281,
20996,
356,
8088,
102,
51285,
33944,
4600,
61853,
4450,
63663,
32487,
22590,
45357,
25566,
56392,
116,
21265,
55532,
4706,
22590,
21251,
1847,
2326,
102,
4600,
51058,
4450,
22590,
30384,
7712,
22103,
7525,
281,
20996,
57020,
51593,
332,
46804,
7104,
2063,
30243,
4811,
52584,
59733,
4706,
22590,
356,
8088,
102,
281,
265
] | [
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1,
1
] |