Tandem sigmatropic rearrangements and cyclizations of propargylic dialkoxy disulfides

Samuel Braverman; Tatiana Pechenick; Hugo E. Gottlieb

doi:10.1016/s0040-4039(02)02653-9

Tandem sigmatropic rearrangements and cyclizations of propargylic dialkoxy disulfides

Samuel Braverman, Tatiana Pechenick, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

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

19 Scopus citations

Abstract

The first successful preparation of propargylic dialkoxy disulfides in high yields is reported. These esters afforded novel 6,7-dithiabicyclo[3.1.1]heptane-2-one 6-oxide derivatives via an unprecedented sequence of three [2,3]- and one [3,3]-sigmatropic shifts followed by an intramolecular [2+2] cycloaddition. The latter are structurally related to the zwiebelanes, recently isolated from freshly cut onion.

Original language	English
Pages (from-to)	777-780
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	4
DOIs	https://doi.org/10.1016/s0040-4039(02)02653-9
State	Published - 20 Jan 2003

Bibliographical note

Funding Information:
The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

Funding

The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

Funders	Funder number
Israel Science Foundation

Keywords

Cycloaddition
Propargylic dialkoxy disulfides
Sigmatropic rearrangement
Sulfine
Synthesis
Thioaldehyde

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10.1016/s0040-4039(02)02653-9

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abstract = "The first successful preparation of propargylic dialkoxy disulfides in high yields is reported. These esters afforded novel 6,7-dithiabicyclo[3.1.1]heptane-2-one 6-oxide derivatives via an unprecedented sequence of three [2,3]- and one [3,3]-sigmatropic shifts followed by an intramolecular [2+2] cycloaddition. The latter are structurally related to the zwiebelanes, recently isolated from freshly cut onion.",

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AU - Pechenick, Tatiana

AU - Gottlieb, Hugo E.

N1 - Funding Information: The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

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N2 - The first successful preparation of propargylic dialkoxy disulfides in high yields is reported. These esters afforded novel 6,7-dithiabicyclo[3.1.1]heptane-2-one 6-oxide derivatives via an unprecedented sequence of three [2,3]- and one [3,3]-sigmatropic shifts followed by an intramolecular [2+2] cycloaddition. The latter are structurally related to the zwiebelanes, recently isolated from freshly cut onion.

AB - The first successful preparation of propargylic dialkoxy disulfides in high yields is reported. These esters afforded novel 6,7-dithiabicyclo[3.1.1]heptane-2-one 6-oxide derivatives via an unprecedented sequence of three [2,3]- and one [3,3]-sigmatropic shifts followed by an intramolecular [2+2] cycloaddition. The latter are structurally related to the zwiebelanes, recently isolated from freshly cut onion.

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KW - Sigmatropic rearrangement

KW - Sulfine

KW - Synthesis

KW - Thioaldehyde

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Tandem sigmatropic rearrangements and cyclizations of propargylic dialkoxy disulfides

Abstract

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