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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 186, 2011 - Issue 5: 24th International Symposium on the Organic Chemistry of Sulfur
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Oral Contributions

Chalcogen Halides Plus Propargyl Alcohols—Fascinating Reaction Pathways and Products

Samuel Braverman Department of Chemistry, Bar-Ilan University, Ramat-Gan, Israel
,
Dr Marina Cherkinsky Department of Chemistry, Bar-Ilan University, Ramat-Gan, Israel
,
Dr Tatiana Pechenick-Azizi Department of Chemistry, Bar-Ilan University, Ramat-Gan, Israel
,
Mrs Yuliya Kalendar Department of Chemistry, Bar-Ilan University, Ramat-Gan, Israel
&
Professor Milon Sprecher Department of Chemistry, Bar-Ilan University, Ramat-Gan, Israel
Pages 1251-1254 | Received 30 Jun 2010, Accepted 07 Jul 2010, Published online: 12 Jul 2011
 
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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.

Acknowledgments

This work was supported by a grant from the Israel Science Foundation (Grant No. 919-05).

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