A novel synthesis of monosubstituted sulfines via an unusual β-elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides

Samuel Braverman; Dan Grinstein; Hugo E. Gottlieb

doi:10.1016/s0040-4039(00)76009-6

A novel synthesis of monosubstituted sulfines via an unusual β-elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides

Samuel Braverman, Dan Grinstein, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

A new method for the synthesis of thioaldehyde S-oxides by base-induced elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. A mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.

Original language	English
Pages (from-to)	953-956
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	6
DOIs	https://doi.org/10.1016/s0040-4039(00)76009-6
State	Published - 1994

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title = "A novel synthesis of monosubstituted sulfines via an unusual β-elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides",

abstract = "A new method for the synthesis of thioaldehyde S-oxides by base-induced elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. A mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.",

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AB - A new method for the synthesis of thioaldehyde S-oxides by base-induced elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. A mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.

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A novel synthesis of monosubstituted sulfines via an unusual β-elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides

Abstract

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