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

RAW Johnstone

Index: Cristiano, M. Lurdes S.; Johnstone, Robert A. W. Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 3 p. 489 - 494

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Citation Number: 27

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.

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