Mechanism of Formation of Grignard Reagents

E. A. Vogler, R. L. Stein, J. M. Hayes

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

Experiment shows that there is no carbon kinetic isotope effect in the formation of CHsMgl from CH3I (k12/k13 = 0.9992, σ = 0.0005). Calculations indicate that an observable isotope effect should accompany this reaction if it proceeds by an inner-sphere electron-transfer mechanism in which breakage of the carbon-halogen bond must be involved in the rate-determining step. Accordingly, it is proposed that the alternative mechanism must be followed, with the rate-determining step involving formation of a radical-ion pair by outer-sphere electron transfer from the magnesium to the organic halide.

Original languageEnglish (US)
Pages (from-to)3163-3166
Number of pages4
JournalJournal of the American Chemical Society
Volume100
Issue number10
DOIs
StatePublished - Jan 1 1978

All Science Journal Classification (ASJC) codes

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

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