Sulfine Chemistry
- 1 May 1989
- journal article
- plenary and-invited-lectures
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 43 (1) , 1-24
- https://doi.org/10.1080/10426508908040276
Abstract
Sulfines (thione S-oxides) are non-linear sulfur-centered heterocumulenes with the general structure XY=SO. In the introduction the various approaches to the synthesis of sulfines and their reactions are briefly reviewed. In a separate section attention is given to the preparation of sulfines using of the reaction of sulfur dioxide with α-silyl carbanions (the modified Peterson reaction). This method provides an access to chiral sulfines, which are interesting partners in asymmetric cycloaddition reactions with dienes. The preparation of α-oxo sulfines from α-methylene ketones, or the corresponding silyl enol ethers, and thionyl chloride is also treated in some detail. These α-oxo sulfines readily undergo cycloaddition reactions with dienes to yield various sulfur-containing heterocycles.Keywords
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