Chalcogen halides plus propargyl alcohols - Fascinating reaction pathways and products

S. Braverman; M. Cherkinsky; T. Pechenick-Azizi; Yu Kalendar; M. Sprecher

doi:10.1080/10426507.2010.507731

Chalcogen halides plus propargyl alcohols - Fascinating reaction pathways and products

S. Braverman, M. Cherkinsky, T. Pechenick-Azizi, Yu Kalendar, M. Sprecher

Department of Chemistry

Bar-Ilan University

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

1 Scopus citations

Abstract

A convenient method to incorporate selenium into an organic molecule is reported. Selenium halides undergo smooth 1,2-addition to the triple bond of various propargylic alcohols under mild reaction conditions and with complete regio-and stereospecificity. The products arising from these reactions depend on the nature of the selenium halide as well as on the substitution pattern of the propargyl alcohol. Of special mechanistic interest is the syn-addition and anti-Markovnikov orientation observed in all cases.

Original language	English
Pages (from-to)	1251-1254
Number of pages	4
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	186
Issue number	5
DOIs	https://doi.org/10.1080/10426507.2010.507731
State	Published - 2011

Bibliographical note

Funding Information:
Received 30 June 2010; accepted 7 July 2010. This work was supported by a grant from the Israel Science Foundation (Grant No. 919-05). Address correspondence to S. Braverman, Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. E-mail: [email protected]

Keywords

Divinyl selenides
Electrophilic addition
Regioselectivity
Selenium dichloride
Selenium tetrachloride
Stereoselectivity

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10.1080/10426507.2010.507731

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title = "Chalcogen halides plus propargyl alcohols - Fascinating reaction pathways and products",

abstract = "A convenient method to incorporate selenium into an organic molecule is reported. Selenium halides undergo smooth 1,2-addition to the triple bond of various propargylic alcohols under mild reaction conditions and with complete regio-and stereospecificity. The products arising from these reactions depend on the nature of the selenium halide as well as on the substitution pattern of the propargyl alcohol. Of special mechanistic interest is the syn-addition and anti-Markovnikov orientation observed in all cases.",

keywords = "Divinyl selenides, Electrophilic addition, Regioselectivity, Selenium dichloride, Selenium tetrachloride, Stereoselectivity",

author = "S. Braverman and M. Cherkinsky and T. Pechenick-Azizi and Yu Kalendar and M. Sprecher",

note = "Funding Information: Received 30 June 2010; accepted 7 July 2010. This work was supported by a grant from the Israel Science Foundation (Grant No. 919-05). Address correspondence to S. Braverman, Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. E-mail: [email protected]",

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AU - Kalendar, Yu

AU - Sprecher, M.

N1 - Funding Information: Received 30 June 2010; accepted 7 July 2010. This work was supported by a grant from the Israel Science Foundation (Grant No. 919-05). Address correspondence to S. Braverman, Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. E-mail: [email protected]

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AB - A convenient method to incorporate selenium into an organic molecule is reported. Selenium halides undergo smooth 1,2-addition to the triple bond of various propargylic alcohols under mild reaction conditions and with complete regio-and stereospecificity. The products arising from these reactions depend on the nature of the selenium halide as well as on the substitution pattern of the propargyl alcohol. Of special mechanistic interest is the syn-addition and anti-Markovnikov orientation observed in all cases.

KW - Divinyl selenides

KW - Electrophilic addition

KW - Regioselectivity

KW - Selenium dichloride

KW - Selenium tetrachloride

KW - Stereoselectivity

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Chalcogen halides plus propargyl alcohols - Fascinating reaction pathways and products

Abstract

Bibliographical note

Keywords

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