Synthesis, rearrangement and solvolysis of propargylic and allylic trifluoromethanesulfinates

Samuel Braverman, Tatiana Pechenick, Yossi Zafrani

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The synthesis and reactivity of propargylic and allylic trifluoromethanesulfinates under various conditions has been investigated. Propargylic esters readily undergo [2,3]-sigmatropic rearrangement to the corresponding allenyl trifluoromethyl sulfones, even under solvolytic conditions. An unusually facile nucleophilic addition of the solvent to the allenyl sulfone under the latter conditions has also been observed. On the other hand, the reactivity of allylic esters strongly depends on substitution. Thus, while cinnamyl triflinate reacts by an ionic mechanism, the corresponding α-methylallyl ester reacts by a concerted pathway.

Original languageEnglish
Pages (from-to)51-63
Number of pages13
JournalArkivoc
Volume2004
Issue number2
DOIs
StatePublished - 2004

Bibliographical note

Publisher Copyright:
© ARKAT USA, Inc.

Keywords

  • Acetylenes
  • Alkenes
  • Allenes
  • Trifloromethyl sulfones
  • Trifluoromethanesulfinates
  • [2,3]-sigmatropic rearrangements

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