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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. and Clegg, W. and MacGregor, M. and Mulvey, Robert and 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). pp. 608-610. ISSN 0022-4936

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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.