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.

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

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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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T2 - solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions

AU - Armstrong, David. R.

AU - Clegg, W.

AU - MacGregor, M.

AU - Mulvey, Robert

AU - O'Neil, P.A.

PY - 1993/4/7

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

SP - 608

EP - 610

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

SN - 0022-4936

IS - 7

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