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

Research output: Contribution to journalArticle

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.

LanguageEnglish
Pages608-610
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Volume1993
Issue number7
DOIs
Publication statusPublished - 7 Apr 1993

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Triazines
Nitriles
Anions
X-Rays
butyllithium
tetrahydrofuran

Keywords

  • organic nitriles
  • lithio triazine
  • dihydrotriazino anions

Cite this

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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.",
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AU - Armstrong, David. R.

AU - Clegg, W.

AU - MacGregor, M.

AU - Mulvey, Robert

AU - O'Neil, P.A.

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Y1 - 1993/4/7

N2 - 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.

AB - 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.

KW - organic nitriles

KW - lithio triazine

KW - dihydrotriazino anions

U2 - 10.1039/C39930000608

DO - 10.1039/C39930000608

M3 - Article

VL - 1993

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EP - 610

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

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