A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones

Abstract

The mechanism of the thermal rearrangement of 1-aryl-5-allyloxytetrazoles 1 to give 1-aryl-4-allyltetrazolones 2 in very high yield has been investigated through kinetic studies in one polar and one less polar solvent. The results suggest mainly a concerted [3,3] sigmatropic process, in which a partially positively charged allyl group migrates from oxygen to nitrogen, similar to the polar transition state found in the Claisen rearrangement.