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

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.