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A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones
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Resumo(s)
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.
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Cristiano, M. Lurdes S.; Johnstone, Robert A. W. A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones, Journal of the Chemical Society, Perkin Transactions 2, 3, 489-494, 1997.