Isotopic labelling in the study of organic and organometallic mechanism and structure: an account

Guy C. Lloyd-Jones, M. Paz Munoz

Research output: Contribution to journalLiterature reviewpeer-review

Abstract

An account of the use of stable isotopes (2 H, C-13, N-15, 180,S-34) for the study of organic and organometallic reaction mechanism and structure, by way of kinetic determinations and modelling, NMR spectroscopy and mass spectrometry is presented. The techniques discussed include use of kinetic isotope effects, label-facilitated nOe experiments, cross-over experiments, stereoisotopochemical analysis, label-facilitated NMR analysis of enantiomers using chiral-shift reagents and NMR in chiral liquid crystal matrices. The reactions in which these tools have been applied are beta-H elimination in Pd-sigma-alkyl complexes, the Bayliss-Hilman reaction, C-H insertion of stable carbenes, ring-closing metathesis reactions, palladium-catalysed hydrosilyation, palladium-catalysed cycloisomerization, anionic thia-Fries rearrangements, synthesis of proton sponges and their nitrogen stereodynamics, and transition metal (Pd, Mo) catalysed allylic alkylation. Copyright (c) 2007 John Wiley & Sons, Ltd.

Original languageEnglish
Pages (from-to)1072-1087
Number of pages16
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume50
Issue number11-12
DOIs
Publication statusPublished - 15 Oct 2007

Keywords

  • isotopic desymmetrization
  • stereochemistry
  • reaction mechanism
  • organometallics
  • catalysis
  • CATALYZED ALLYLIC ALKYLATION
  • N,N-CHIRAL PROTON SPONGE
  • BAYLIS-HILLMAN REACTION
  • ENYNE METATHESIS
  • ASYMMETRIC ALKYLATION
  • CYCLOISOMERIZATION
  • MOLYBDENUM
  • COMPLEXES
  • 1,6-DIENE
  • CARBENES

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