The 2-(trimethylsilyl)ethyl sulfur group in synthesis

Abstract

The trimethylsilylethyl sulfur group present in 2-(trimethylsilyl)ethyl sulfides, sulfones, sulfoxides and in 2-(trimethylsilyl)ethylsulfonamido derivatives has proved its potential in synthesis. Presence of sulfur and silicon on adjacent carbon atoms provides routes for preparing interesting sulfur or non-sulfur, silicon or non-silicon derivatives like thiols, methyl disulfides, thioesters, thiocyanates, unsaturated derivatives and amines through the selective removal of the trimethylsilylethyl or the trimethylsilyl group. 1 Introduction 2 Synthesis and Reactions of 2-(Trimethylsilyl)ethyl Sulfides 2.1 Synthesis of 2-(Trimethylsilyl)ethanethiol and Derivatives 2.2 Reactions of 2-(Trimethylsilyl)ethyl Sulfides 2.2.1 Synthesis of Non-silylated Thiols and Disulfides 2.2.2 Other Reactions of 2-(Trimethylsilyl)ethyl Sulfides 2.2.2.1 Synthesis of 2-(Trimethylsilyl)ethyl Sulfinimides 2.2.2.2 Removal of the 2-(Trimethylsilyl)ethyl Group and Synthesis of Sulfur Derivatives 3.2-(Trimethylsilyl)ethyl Sulfones and Sulfoxides 3.1 Sulfones 3.2 Sulfoxides 4.2-(Trimethylsilyl)ethylsulfonamido Derivatives 4.1 The 2-(Trimethylsilyl)ethylsulfonamido Protecting Group 4.2 2-(Trimethylsilyl)ethylsulfonamide (SES-NH2) 4.3 The SES-NH-Boc Derivative 4.4 N-Sulfinyl-[2-(trimethylsilyl)ethyl]sulfonamide (SES-NSO) 4.5 Di[2-(trimethylsilyl)ethyl] sulfodiimide 4.6 Other Reagents for the Synthesis of SES-protected Amines 5 Conclusion.