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

doi:10.1039/C39930000608

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

29 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 language	English
Pages (from-to)	608-610
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Volume	1993
Issue number	7
DOIs	https://doi.org/10.1039/C39930000608
Publication status	Published - 7 Apr 1993

Keywords

organic nitriles
lithio triazine
dihydrotriazino anions

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10.1039/C39930000608

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Armstrong, D. R., Clegg, W., MacGregor, M., Mulvey, R., & O'Neil, P. A. (1993). Butyllithium-induced cyclotrimerisation reactions of organic nitriles: solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions . Journal of the Chemical Society, Chemical Communications, 1993(7), 608-610. https://doi.org/10.1039/C39930000608

Armstrong, David. R. ; Clegg, W. ; MacGregor, M. et al. / Butyllithium-induced cyclotrimerisation reactions of organic nitriles : solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions . In: Journal of the Chemical Society, Chemical Communications. 1993 ; Vol. 1993, No. 7. pp. 608-610.

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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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Armstrong, DR, Clegg, W, MacGregor, M, Mulvey, R & O'Neil, PA 1993, 'Butyllithium-induced cyclotrimerisation reactions of organic nitriles: solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions ', Journal of the Chemical Society, Chemical Communications, vol. 1993, no. 7, pp. 608-610. https://doi.org/10.1039/C39930000608

Butyllithium-induced cyclotrimerisation reactions of organic nitriles: solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions . / Armstrong, David. R.; Clegg, W.; MacGregor, M. et al.
In: Journal of the Chemical Society, Chemical Communications, Vol. 1993, No. 7, 07.04.1993, p. 608-610.

Research output: Contribution to journal › Article › peer-review

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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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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

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DO - 10.1039/C39930000608

M3 - Article

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VL - 1993

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JO - Journal of the Chemical Society, Chemical Communications

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Armstrong DR, Clegg W, MacGregor M, Mulvey R, O'Neil PA. Butyllithium-induced cyclotrimerisation reactions of organic nitriles: solvent dependency, crystal and solution structures of lithio triazine intermediates and an unexpected rearrangement of dihydrotriazino anions . Journal of the Chemical Society, Chemical Communications. 1993 Apr 7;1993(7):608-610. doi: 10.1039/C39930000608