Reaction of selenium and tellurium halides with propargyl alcohols. the regio- and stereoselectivity of addition to the triple bond

Samuel Braverman, Marina Cherkinsky, Ranjan Jana, Yuliya Kalendar, Milon Sprecher

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

A convenient method to incorporate selenium into an organic molecule is reported. Various aspects of the reaction of SeCl2 with propargyl alcohols, i.e., identity of reacting functionality, regiospecificity, and stereospecificity, differ from expectations based on known reactions of these alcohols with SCl2. Selenium dihalides undergo smooth 1,2-addition to the triple bond of various propargylic alcohols resulting in the formation of the corresponding functionalized divinyl selenides in high yields and with complete regio- and stereospecificity. Of special mechanistic interest is the syn-addition and anti-Markovnikov orientation observed in all cases.

Original languageEnglish
Pages (from-to)1114-1120
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume23
Issue number11
DOIs
StatePublished - Nov 2010

Keywords

  • alkynes
  • divinyl selenides
  • electrophilic addition
  • regioselectivity
  • selenium dichloride
  • stereoselectivity

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