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

Cristiano, Maria Lurdes Santos; Johnstone, Robert A. W.

http://hdl.handle.net/10400.1/4256

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Authors

Cristiano, Maria Lurdes Santos

Johnstone, Robert A. W.

Abstract(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.

URI

http://hdl.handle.net/10400.1/4256

Citation

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.