N-phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides

被引：86

作者：

Christoforou, Angelos ^{[1
]}

Nicolaou, Georgia ^{[1
]}

Elemes, Yiannis ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, GR-45110 Ioannina, Greece

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 52期

关键词：

N-phenyltriazolinedione; oxidation; thiols; disulfides;

D O I：

10.1016/j.tetlet.2006.10.134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Phenyltriazolinedione is an efficient and chemoselective reagent for the oxidation of thiols to their corresponding symmetrical disulfides. The method is applicable to aromatic, aliphatic, and bi-functional thiols. The one-pot reaction takes a few minutes (in most cases studied) for completion and after a simple work-up affords the corresponding symmetrical disulfides in very good to excellent yields. Furthermore, the reaction could be performed with the same results in the absence of solvent for liquid thiols. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：9211 / 9213

页数：3

共 64 条

[1] SYNTHESIS OF THE 1ST ALPHA-METHYLENE-BETA-PEROXYLACTONE - REGIOSPECIFIC ENE REACTION OF O-1(2) WITH ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS [J].

ADAM, W ;

GRIESBECK, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (12) :1070-1071

[2]

ADAM W, 1990, LIEBIGS ANN CHEM, P1051

[3]

AKASAKA T, 1984, TETRAHEDRON LETT, V25, P4757, DOI 10.1016/S0040-4039(01)81511-2

[4] Oxidation of thiols to disulfides with monochloro poly(styrenehydantoin) beads [J].

Akdag, Akin ;

Webb, Thomas ;

Worley, S. D. .

TETRAHEDRON LETTERS, 2006, 47 (21) :3509-3510

[5] 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

[6] A NEW PROCEDURE FOR THE CONVERSION OF THIOLS INTO REACTIVE SULFENYLATING AGENTS [J].

BARTON, DHR ;

HESSE, RH ;

OSULLIVAN, AC ;

PECHET, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6697-6702

[7] TRIAZOLINEDIONES - CONVERSION TO DEAZA DIMERS BY ELECTRON-TRANSFER CATALYSIS - A POSSIBLE RADICAL-ANION DIELS-ALDER REACTION [J].

BORHANI, DW ;

GREENE, FD .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1563-1570

[8] DISULFIDES .1. SYNTHESES USING 2,2'-DITHIOBIS(BENZOTHIAZOLE) [J].

BRZEZINSKA, E ;

TERNAY, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8239-8244

[9]

CAPOZZI G, 1974, CHEM THILL GROUP 2

[10]

COOKSON RC, 1966, J CHEM SOC CHEM COMM, P744

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