E,Z-Isomers of 3-ethoxy-4,4,4-trifluorobut-2-enenitrile and N-methylpyrrolidines derived from them


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Abstract

3-Ethoxy-4,4,4-trifluorobut-2-enenitrile was synthesized by the Wittig reaction of ethyl trifluoroacetate and (cyanomethylidene)triphenylphosphorane and was separated to individual E- and Z-isomers by rectification. Each isomer undergoes stereospecific 1,3-dipolar cycloaddition to N-methyl(methaniminio)-N-methylide generated in situ to give E- and Z-isomers of 4-cyano-3-ethoxy-3-trifluoromethyl-1-methylpyrrolidine.

About the authors

A. Yu. Volkonskii

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Author for correspondence.
Email: volkonskii@ineos.ac.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991

A. S. Peregudov

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: volkonskii@ineos.ac.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991

T. V. Strelkova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: volkonskii@ineos.ac.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991

N. D. Kagramanov

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: volkonskii@ineos.ac.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991


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