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Synlett 2005(10): 1509-1520  
DOI: 10.1055/s-2005-869847
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© Georg Thieme Verlag Stuttgart · New York

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Toshiaki Murai*
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
e-Mail: mtoshi@cc.gifu-u.ac.jp;
Further Information

Publication History

Received 1 November 2004
Publication Date:
12 May 2005 (online)

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Abstract

This review describes the synthesis and reactions of selenothioic acid S-esters and diselenoic acid esters. Synthetic work with these substances has provided observations, which have led to a proposal about factors that effect their stability. A survey shows that aliphatic derivatives of selenothioic acid S-esters, although being stable compounds, are highly reactive with various electrophilic and nucleophilic reagents. In addition, α-protons in these esters have high acidities. Studies have shown that the chemistry of these esters can be utilized in the synthesis of new types of organoselenium compounds.

1 Introduction

2 Synthesis

2.1 Synthesis via Selenoketene Intermediates

2.2 Synthesis via Selenoic Acid O-Esters

3 Spectroscopic Properties

4 Reactions

4.1 Electrophilic Reactions

4.2 Nucleophilic Reactions

4.3 Concerted Reactions

4.4 Reactions via Eneselenolates

5 Summary

Key words

selenothioic acid S-esters - diselenoic acid esters - organoselenium compounds - selenium-containing heterocycles