Base catalyzed [2,3]-sigmatropic rearrangements of propargylic sulfonium and selenonium salts

Samuel Braverman; Yossi Zafrani; Shai Rahimipour

doi:10.1016/S0040-4039(01)00322-7

Base catalyzed [2,3]-sigmatropic rearrangements of propargylic sulfonium and selenonium salts

Samuel Braverman, Yossi Zafrani, Shai Rahimipour

Department of Chemistry

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

11 Scopus citations

Abstract

The synthesis and reactivity of bis-γ-substituted and unsubstituted propargylic sulfonium and selenonium salts under various basic conditions have been investigated. While the former compounds reacted only by [2,3]-sigmatropic rearrangement of the corresponding sulfur ylides, the latter salts exhibited a wider range of reactivity and showed potent DNA-cleaving properties.

Original language	English
Pages (from-to)	2911-2914
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(01)00322-7
State	Published - 9 Apr 2001

Bibliographical note

Funding Information:
Financial support of this work by the Israel Science Foundation is gratefully acknowledged.

Funding

Financial support of this work by the Israel Science Foundation is gratefully acknowledged.

Funders	Funder number
Israel Science Foundation

Keywords

Acetylenes
Allenes
Sigmatropic rearrangements
Sulfur and selenium compounds

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10.1016/S0040-4039(01)00322-7

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abstract = "The synthesis and reactivity of bis-γ-substituted and unsubstituted propargylic sulfonium and selenonium salts under various basic conditions have been investigated. While the former compounds reacted only by [2,3]-sigmatropic rearrangement of the corresponding sulfur ylides, the latter salts exhibited a wider range of reactivity and showed potent DNA-cleaving properties.",

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AU - Braverman, Samuel

AU - Zafrani, Yossi

AU - Rahimipour, Shai

N1 - Funding Information: Financial support of this work by the Israel Science Foundation is gratefully acknowledged.

PY - 2001/4/9

Y1 - 2001/4/9

N2 - The synthesis and reactivity of bis-γ-substituted and unsubstituted propargylic sulfonium and selenonium salts under various basic conditions have been investigated. While the former compounds reacted only by [2,3]-sigmatropic rearrangement of the corresponding sulfur ylides, the latter salts exhibited a wider range of reactivity and showed potent DNA-cleaving properties.

AB - The synthesis and reactivity of bis-γ-substituted and unsubstituted propargylic sulfonium and selenonium salts under various basic conditions have been investigated. While the former compounds reacted only by [2,3]-sigmatropic rearrangement of the corresponding sulfur ylides, the latter salts exhibited a wider range of reactivity and showed potent DNA-cleaving properties.

KW - Acetylenes

KW - Allenes

KW - Sigmatropic rearrangements

KW - Sulfur and selenium compounds

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Base catalyzed [2,3]-sigmatropic rearrangements of propargylic sulfonium and selenonium salts

Abstract

Bibliographical note

Funding

Keywords

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