Tetrahedron letters

Oxidation of thiol by 5-arylidene 1, 3-dimethylbarbituric acid and its application to synthesis of unsymmetrical disulfide

K Tanaka, X Chen, T Kimura, F Yoneda

Index: Tanaka, Kiyoshi; Chen, Xing; Kimura, Teiji; Yoneda, Fumio Tetrahedron Letters, 1987 , vol. 28, # 36 p. 4173 - 4176

Full Text: HTML

Citation Number: 23

Abstract

Abstract Oxidation of both aromatic and aliphatic thiols by 5-arylidene 1, 3-dimethylbarbituric acid was found to proceed readily to give disulfides in good yield with concomitant reduction of the oxidant to the dihydro compound. Thiol adduct of the dihydro compound was successfully applied to the synthesis of unsymmetrical disulfide under mild conditions in an excellent yield.

Related Articles:

Free radical alkylthiylation of hydridophosphoranes. Structure-reactivity factors affecting the reactions of bicyclic phosphoranyl radicals with disulfides

[Bentrude,W.G.; Kawashima,T.; Keys,B.A. Journal of the American Chemical Society, 1987 , vol. 109, p. 1227]

Facile synthesis of alkylthiophosphonium salts of tris (2, 6-dimethoxyphenyl) phosphine and their reactions with thiols.

[Wada, Masanori; Kanzaki, Mituyuki; Fujiwara, Masanobu; Kajihara, Kazuhisa; Erabi, Tatsuo Chemistry Letters, 1990 , # 6 p. 867 - 870]

Reaction of 2-(alkylsulfinyl)-, 2-(arylsulfinyl)-, and 2-(aralkylsulfinyl) benzimidazoles with thiols: a convenient synthesis of unsymmetrical disulfides

[Graber, David R.; Morge, Raymond A.; Sih, John C. Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4620 - 4622]

Facile reduction of sulfinic acid to disulfide with thiol and chlorotrimethylsilane

[Oae, Shigeru; Togo, Hideo; Numata, Tatsuo; Fujimori, Ken Chemistry Letters, 1980 , p. 1193 - 1196]

Reaction of 2-(alkylsulfinyl)-, 2-(arylsulfinyl)-, and 2-(aralkylsulfinyl) benzimidazoles with thiols: a convenient synthesis of unsymmetrical disulfides

[Graber, David R.; Morge, Raymond A.; Sih, John C. Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4620 - 4622]

More Articles...