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Synthesis of mono- and disubstituted sulfines via β-elimination of chloroform from trichloromethyl sulfoxides

✍ Scribed by Samuel Braverman; Dan Grinstein; Hugo E. Gottlieb

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
729 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new method for the synthesis of thioaldehyde and thioketone S-oxides by an unusual base-induced I~-elimination of chloroform from readily available aUylic and bcnzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. The facile preparation of cx,13-unsaturated sulfines by the new method is of special interest. A possible mechanism for this remarkable sulfine synthesis and apparently unprecedented 13-elimination of chloroform is presented.

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