Butyllithium-induced cyclotrimerisation reactions of organic nitriles: solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions

David. R. Armstrong, W. Clegg, M. MacGregor, Robert Mulvey, P.A. O'Neil

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27 Citations (Scopus)

Abstract

Sequential addition of Bu(t)C=N and PhC=N (2 equiv.) to Bu(n)Li in the presence of tetrahydrofuran (THF) produces an isolable lithio 1,4-dihydrotriazine tris(THF)solvate, characterised by both NMR spectroscopic and X-ray crystallographic methods, which converts to a 1,2-dihydro arrangement on methanolysis.

Original languageEnglish
Pages (from-to)608-610
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Volume1993
Issue number7
DOIs
Publication statusPublished - 7 Apr 1993

Keywords

  • organic nitriles
  • lithio triazine
  • dihydrotriazino anions

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