Reactivity of fulvenes. Nucleophilic displacement by piperi 6-p-tolysulphonyloxyfulvene

Abstract

The reaction of 6-p-tolylsulphonyloxyfulvene with piperidine in several solvents has been followed ki means of the stopped-flow technique. The high reactivity observed is attributed to the intervention mediate which involves delocalization of the negative charge into the five-membered ring. The lack by the reacting amine, the absence of an isotope effect when N-deuteriopiperidine is the reagent, and otltions lead to the conclusion that the formation of the intermediate is rate determining and its decompos in a fast step.