Tandem carbon-carbon and carbon-chlorine bond formation by Cu(II) chloride-promoted [3,3] sigmatropic rearrangement of N-allylhydrazones

Devon A. Mundal, Jennifer J. Lee, Regan James Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

A new copper(II) chloride-promoted rearrangement of N-allylhydrazones has been developed. Treatment of a number of aromatic N-allylhydrazones with copper(II) chloride provides the formation of both a new carbon-carbon bond and a carbon-chlorine bond in the same reaction. Substrate studies revealed that the carbon-carbon bond-forming step proceeds by way of a concerted [3,3] sigmatropic rearrangement and selectively generates trans-substituted alkenes.

Original languageEnglish (US)
Pages (from-to)1148-1149
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number4
DOIs
StatePublished - Jan 30 2008

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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