Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines |
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Authors: | A S Konev M S Novikov A F Khlebnikov |
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Institution: | (1) St. Petersburg State University, St. Petersburg, 19850, Russia |
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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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