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1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Schiff Bases and Difluorocarbene to Symmetric Olefins

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Abstract

Difluoro(iminio)methanides generated by the action of difluorocarbene on Schiff bases react with derivatives of maleic and fumaric acids, following the 1,3-dipolar cycloaddition pattern to give 2,2-difluoropyrrolidines which were detected by gas chromatography-mass spectrometry. The final products are stereo-isomeric substituted 2-pyrrolidinones formed by hydrolysis of difluoropyrrolidines and their dehydrofluorination products, 2-fluoro-4,5-dihydropyrroles. The observed stereoselectivity of the cycloaddition suggests Z configuration of intermediate ylide and both endo- and exo-approach to the dipolarophile in the transition state corresponding to cycloaddition.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    M. S. Novikov, A. F. Khlebnikov, E. S. Sidorina, A. E. Masalev & R. R. Kostikov

  2. Institut für Anorganische Chemie, Hamburg, Germany

    J. Kopf

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  1. M. S. Novikov
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  2. A. F. Khlebnikov
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  3. E. S. Sidorina
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Novikov, M.S., Khlebnikov, A.F., Sidorina, E.S. et al. 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Schiff Bases and Difluorocarbene to Symmetric Olefins. Russian Journal of Organic Chemistry 38, 672–682 (2002). https://doi.org/10.1023/A:1019659021891

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