Solvolytic rearrangements of azabicyclic compounds. Part 2. Kinetics

Abstract

Rates of solvolysis in aqueous ethanol and aqueous dioxan of three 2-exo-chloroazabicycloalkanes have been studied and first-order rate constants are derived and compared with published values for analogous compounds. Anchimeric assistance by the bridge N-atom is evidently not important in the rate-controlling step in these rearrangements, though it may occur to a minor extent in the case of 2-exo-chloro-7-methyl-7-azanorbornane. Solvolytic results for tropan-2β-yl toluene-p-sulphonate in aqueous ethanol and aqueous acetone mixtures are also reported and compared with literature data for the carbobicyclic and oxabicyclic analogues.