Simple, extremely fast, and high-yielding oxidation of thiols to disulfides

被引：37

作者：

Alam, A ^{[1
]}

Takaguchi, Y ^{[1
]}

Tsuboi, S ^{[1
]}

机构：

[1] Okayama Univ, Fac Environm Sci & Technol, Dept Environm Chem & Mat, Okayama 7008530, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 10期

关键词：

1,3-dibromo-5,5-dimethylhydantoin; disulfides; oxidation of thiols;

D O I：

10.1081/SCC-200057253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Results of oxidation of thiols to disulfides with 1,3-dibromo-5,5-dimethyl-hydantoin (DBDMH) are described. A simple addition of 0.20-0.25mol equivalent of solid DBDMH to thiol in chloroform at room temperature yielded the disulfides in excellent yield. The reaction is extremely fast and gave no other oxidized side products.

引用

页码：1329 / 1333

页数：5

共 23 条

[1] Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support [J].

Ali, MH ;

McDermott, M .

TETRAHEDRON LETTERS, 2002, 43 (35) :6271-6273

[2] Zinc-bound thiolate-disulfide exchange:: A strategy for inhibiting metallo-β-lactamases [J].

Boerzel, H ;

Koeckert, M ;

Bu, WM ;

Spingler, B ;

Lippard, SJ .

INORGANIC CHEMISTRY, 2003, 42 (05) :1604-1615

[3]

CHRISTENSEN WL, 1978, SYNTHESIS-STUTTGART, V1, P50

[4]

Cremlyn R. J., 1996, INTRO ORGANOSULFUR C

[5] KINETICS AND MECHANISM OF THE OXIDATION OF NORMAL-DODECANETHIOL AND PYRIDINE-SUBSTITUTED ETHANETHIOLS BY I2 IN ACETONITRILE [J].

DELEEUW, DL ;

MUSKER, WK ;

DOI, JT .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4860-4864

[6]

DHAR DN, 1984, INDIAN J CHEM B, V23, P974

[7]

DRABOWICZ J, 1980, SYNTHESIS-STUTTGART, P32

[8]

FIROUZABADI H, 1983, SYNTHETIC COMMUN, V13, P611, DOI 10.1080/00397918308059536

[9]

Firouzabadi H., 1988, SULFUR LETT, V61, P2185

[10] Trimethylchlorosilane (TMSCl) and cyanuric chloride (CC) catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide [J].

Karimi, B ;

Hazarkhani, H ;

Zareyee, D .

SYNTHESIS-STUTTGART, 2002, (17) :2513-2516

← 1 2 3 →