A convenient preparation of mixed allylic and allenic thiosulfinates

Samuel Braverman; Tatiana Pechenick; Hugo E. Gottlieb; Milon Sprecher

doi:10.1016/j.tetlet.2004.09.017

A convenient preparation of mixed allylic and allenic thiosulfinates

Samuel Braverman, Tatiana Pechenick, Hugo E. Gottlieb, Milon Sprecher

Department of Chemistry

Bar-Ilan University

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

7 Scopus citations

Abstract

The first successful preparation of propargylic and allylic chloroalkoxy disulfides in high yields is reported. Facile 1,4-electrophilic addition of these to 2,3-dimethyl-1,3-butadiene, followed by [2,3]-sigmatropic rearrangements affords mixed allyl allenic and bis-allylic thiosulfinates, respectively. Due to their similarity to allicin, the latter are of potential biological interest.

Original language	English
Pages (from-to)	8235-8238
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.017
State	Published - 25 Oct 2004

Bibliographical note

Funding Information:
This research was supported by The Israel Science Foundation (Grant No 280/01-1).

Funding

This research was supported by The Israel Science Foundation (Grant No 280/01-1).

Funders	Funder number
Israel Science Foundation	280/01-1

Keywords

Alkenes
Alkynes
Allenes
Chloroalkoxy disulfides
Thiosulfinates
[2,3]-Sigmatropic rearrangements

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10.1016/j.tetlet.2004.09.017

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title = "A convenient preparation of mixed allylic and allenic thiosulfinates",

abstract = "The first successful preparation of propargylic and allylic chloroalkoxy disulfides in high yields is reported. Facile 1,4-electrophilic addition of these to 2,3-dimethyl-1,3-butadiene, followed by [2,3]-sigmatropic rearrangements affords mixed allyl allenic and bis-allylic thiosulfinates, respectively. Due to their similarity to allicin, the latter are of potential biological interest.",

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author = "Samuel Braverman and Tatiana Pechenick and Gottlieb, {Hugo E.} and Milon Sprecher",

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T1 - A convenient preparation of mixed allylic and allenic thiosulfinates

AU - Braverman, Samuel

AU - Pechenick, Tatiana

AU - Gottlieb, Hugo E.

AU - Sprecher, Milon

N1 - Funding Information: This research was supported by The Israel Science Foundation (Grant No 280/01-1).

PY - 2004/10/25

Y1 - 2004/10/25

N2 - The first successful preparation of propargylic and allylic chloroalkoxy disulfides in high yields is reported. Facile 1,4-electrophilic addition of these to 2,3-dimethyl-1,3-butadiene, followed by [2,3]-sigmatropic rearrangements affords mixed allyl allenic and bis-allylic thiosulfinates, respectively. Due to their similarity to allicin, the latter are of potential biological interest.

AB - The first successful preparation of propargylic and allylic chloroalkoxy disulfides in high yields is reported. Facile 1,4-electrophilic addition of these to 2,3-dimethyl-1,3-butadiene, followed by [2,3]-sigmatropic rearrangements affords mixed allyl allenic and bis-allylic thiosulfinates, respectively. Due to their similarity to allicin, the latter are of potential biological interest.

KW - Alkenes

KW - Alkynes

KW - Allenes

KW - Chloroalkoxy disulfides

KW - Thiosulfinates

KW - [2,3]-Sigmatropic rearrangements

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SN - 0040-4039

VL - 45

SP - 8235

EP - 8238

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

A convenient preparation of mixed allylic and allenic thiosulfinates

Abstract

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Keywords

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