Synthesis and Reaction of 1-Azabicyclo[3.1.0]hexane

Abstract

The effective formation of 1-azabicyclo[3.1.0]hexane (5) by treatment of 2-(bromomethyl)pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on intermolecular Br···Li⁺ coordination (SN2 process). The reaction of 5 with electrophiles 13a—n gave the corresponding pyrrolidines 14a—n and piperidine 6, 15a—g, i—n. The selectivity of the products in this reaction appeared to be controlled by equilibrium.