The mechanism of lithiation and nitrile insertion reactions of β-methylazines: Evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA

Sarah C. Ball, Robert P. Davies, Paul R. Raithby, Gregory P. Shields, Ronald Snaith

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction of 1:LDA:PhCN is carried out, suggest a mechanism for previously published cyclisation reactions of β-methylazines.

Original languageEnglish
Pages (from-to)457-461
Number of pages5
JournalJournal of Organometallic Chemistry
Volume550
Issue number1-2
DOIs
Publication statusPublished - 15 Jan 1998

Keywords

  • Lithium
  • Nitriles
  • Reaction mechanisms
  • X-ray structure

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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