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

Samuel Braverman; Dan Grinstein; Hugo E. Gottlieb

doi:10.1016/s0040-4020(97)00904-6

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

Samuel Braverman, Dan Grinstein, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

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

13 Scopus citations

Abstract

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

Original language	English
Pages (from-to)	13933-13944
Number of pages	12
Journal	Tetrahedron
Volume	53
Issue number	40
DOIs	https://doi.org/10.1016/s0040-4020(97)00904-6
State	Published - 6 Oct 1997

Bibliographical note

Funding Information:
Acknowledgment: This work was supported by a grant from the ISRAEL SCIENCE FOUNDATION.

Funding

Acknowledgment: This work was supported by a grant from the ISRAEL SCIENCE FOUNDATION.

Funders	Funder number
Israel Science Foundation

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10.1016/s0040-4020(97)00904-6

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abstract = "A new method for the synthesis of thioaldehyde and thioketone S-oxides by an unusual base-induced β-elimination of chloroform from readily available allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. The facile preparation of α,β-unsaturated sulfines by the new method is of special interest. A possible mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.",

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AU - Grinstein, Dan

AU - Gottlieb, Hugo E.

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PY - 1997/10/6

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N2 - A new method for the synthesis of thioaldehyde and thioketone S-oxides by an unusual base-induced β-elimination of chloroform from readily available allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. The facile preparation of α,β-unsaturated sulfines by the new method is of special interest. A possible mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.

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

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

Abstract

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