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Synthesis 2007(18): 2755-2778
DOI: 10.1055/s-2007-983883
DOI: 10.1055/s-2007-983883
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Reactions of 2-Alkylidene Thiiranes and Thietanes
Further Information
Received
21 March 2007
Publication Date:
29 August 2007 (online)
Publication History
Publication Date:
29 August 2007 (online)
Abstract
This review covers the synthesis and applications of three- and four-membered sulfur-containing rings with adjacent exocyclic unsaturation. Alkylidene thiiranes have been of largely theoretical interest with few applications. Conversely, alkylidene thietanes and dithietanes have been used as intermediates for the synthesis of a number of heterocyclic ring systems. Publications related to both systems peaked a number of years ago, but it is hoped that this review will stimulate interest and lead to new research in these areas.
1 Introduction
2 Alkylidene Thiiranes (Allene Episulfides)
2.1 Miscellaneous Preparations
2.2 Preparations from Diazolines
2.3 Reactions
3 2-Alkylidene Thietanes and Dithietanes
3.1 Monoalkylidene Thietanes
3.2 Monoalkylidene Dithietanes
3.3 Dialkylidene Dithietanes (Desaurins)
3.3.1 Preparations
3.3.2 Reactions
4 Conclusions
Key words
thiiranes - thietanes - dithietanes - alkylidene - strained heterocycles
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