Chalcogen halides plus propargyl alcohols - Fascinating reaction pathways and products

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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)1251-1254
Number of pages4
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume186
Issue number5
DOIs
StatePublished - 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: bravers@mail.biu.ac.il

Keywords

  • Divinyl selenides
  • Electrophilic addition
  • Regioselectivity
  • Selenium dichloride
  • Selenium tetrachloride
  • Stereoselectivity

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