Brominated vinyl ketene thioacetal, ene- and diene acetals; potential four-carbon synthons

Samuel Braverman, Marina Cherkinsky, Eliahu Nov, Milon Sprecher

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A novel and convenient procedure for the preparation of conjugated vinyl ketene thioacetals is described: it involves addition of CBr4 to acrolein, followed by thioacetalization of the corresponding aldehyde 2 and double dehydrobromination of 3 under basic conditions for comparison, three O- acetals 4-6 were also prepared. In contrast to the reaction of dithioacetal 3, these acetals undergo either a single or double HBr elimination with formation of mono-olefins or cumulated diene, respectively. The mechanism of formation of the reaction products is discussed, and the reactivity of the novel per-functionalized tetrasubstituted 1,3-butadiene 1 with the strongly electrophilic dienophile PTAD is presented.

Original languageEnglish
Pages (from-to)2353-2362
Number of pages10
JournalTetrahedron
Volume55
Issue number8
DOIs
StatePublished - 19 Feb 1999

Keywords

  • Acetals
  • Dithiolane
  • Elimination reactions
  • Thioacetals

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