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Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

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Abstract

N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-π-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dimethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-π-cyclization, in the presence of acid catalysts suffer isomerization into α-fluoroimines and 1,3-disubstituted indoles.

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 19850, Russia

    A. S. Konev, M. S. Novikov & A. F. Khlebnikov

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  1. A. S. Konev
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  2. M. S. Novikov
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  3. A. F. Khlebnikov
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Original Russian Text © A.S. Konev, M.S. Novikov, A.F. Khlebnikov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 2, pp. 292–302.

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Konev, A.S., Novikov, M.S. & Khlebnikov, A.F. Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines. Russ J Org Chem 43, 286–296 (2007). https://doi.org/10.1134/S1070428007020224

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  • DOI: https://doi.org/10.1134/S1070428007020224

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