Unexpected thorpe reaction of an α-alkoxynitrile

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Abstract

α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at -78°C gave the dimer 5 instead of the expected C1(-elongated product 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. Scrutinizing the 1H NMR spectra revealed that the enamine tautomer 5b is predominant over the imine 5a in the solvents investigated.

Original languageEnglish
Pages (from-to)127-131
Number of pages5
JournalMolecules
Volume5
Issue number2
DOIs
Publication statusPublished - Feb 2000

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Keywords

  • Self-condensation
  • Thorpe reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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