Recent Developments in Disulfide
Bond Formation

Dariusz Witt

doi:10.1055/s-2008-1067188

REVIEW

Recent Developments in Disulfide Bond Formation

Dariusz Witt*
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: dwitt@chem.pg.gda.pl;

Abstract

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Abstract

This review summarizes the recent developments of disulfide bond formation with a variety of reagents. The scope and limitations of the presented methods are discussed. The syntheses of unsymmetrical disulfides are highlighted in order to present the most versatile achievements.

1 Introduction

2 Preparation of Disulfides

2.1 By Oxidation of Thiols

2.2 By Reductive Coupling of Sulfonyl Chlorides

2.3 By Reaction with Sulfur Monochloride

2.4 By Radical Cyclization of Substituted Aminothiourea Derivatives

2.5 Using 1-Chlorobenzotriazole

2.6 From Elemental Sulfur

2.7 From Organophosphorus Sulfenyl Bromide

2.8 From N-Trifluoroacetyl Arenesulfenamides

2.9 Using Phase-Transfer Catalysis

2.10 From a Thiol-Disulfide Exchange Reaction

2.11 From Thiocyanates

2.12 From 2-(Trimethylsilyl)ethyl Sulfides

2.13 From Thiosulfonates and Thiosulfates

2.14 From Thioesters

2.15 By Disulfide Exchange Reactions

2.16 From Tetrathiomolybdate

2.17 By Miscellaneous Reactions

3 Conclusions

Key words

disulfides - thiols - synthesis - symmetrical disulfides - unsymmetrical disulfides

Full Text

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