Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

Paul Davies, N Martin, Neil Spencer

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using C-13-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of C-13- and deuterium-labelled substrates.
Original languageEnglish
Pages (from-to)839-846
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume7
DOIs
Publication statusPublished - 1 Jun 2011

Keywords

  • isotopic labelling
  • cycloisomerisation
  • skeletal rearrangement
  • pyrrole
  • gold
  • 1,2-aryl shift

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