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DOI: 10.1039/A603191I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 643-648

Ring cleavage of 1-alkyl-2-aryl-3-(hydroxymethyl)pyrrolidines. A PM3 semiempirical study of molecular mechanism

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Eugenia González Rosende, Luis R. Domingo, José Sepúlveda-Arques, Dolores Perona Mármol, Elena Zaballos García, Alberto Acero-Alarcón and Belén Yruretagoyena Solesio

Abstract

A fragmentation reaction at room temperature takes place when 2-aryl-3-(hydroxymethyl)-1-methylpyrrolidines react with different arenesulfonyl chlorides and triethylamine. A PM3 semiempirical study of the fragmentation reaction of the quaternary benzenesulfonamide salt of 1-methyl-2-phenyl-3-(hydroxymethyl)pyrrolidine shows that the reaction proceeds by a stepwise mechanism through the formation of a benzylic cation.

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