Synthesis and reactivity of divinylselenium dichlorides and dibromides

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

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Regio- and stereospecific electrophilic addition reactions of selenium tetrachloride and selenium tetrabromide to propargyl alcohols are reported. (Z,Z)-Bis(β-chlorovinyl)selenium dichlorides were isolated in high yields, and their reactivity was dependent on their substitution pattern. Products derived from unsubstituted, α-methyl-, or α, α- dimethylpropargyl alcohols readily underwent transfer of chlorine atoms to one of the two double bonds. (Z,Z)-Bis(β-chlorovinyl)selenium dichlorides derived from γ-phenyl- or γ-isopropenylpropargyl alcohols underwent cyclization to form benzoselenophene derivatives; this was accompanied by the formation of the corresponding dichloro-substituted allylic alcohols. In contrast, selenium tetrachloride reacts with γ-phenylpropargyl alcohol exclusively as a chlorinating agent, giving (3-chloroprop-1-yn-1-yl)benzene quantitatively. Products of regio- and stereospecific electrophilic addition of selenium tetrabromide are also described. Reaction mechanisms are proposed.

Original languageEnglish
Article numberP17010SS
Pages (from-to)577-584
Number of pages8
JournalSynthesis
Issue number4
DOIs
StatePublished - 2011

Keywords

  • alcohols
  • alkynes
  • electrophilic additions
  • halides
  • selenium

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