Oxime rearrangements: ab initio calculations and reactions in the solid state

V Šimunić-Mežnarić, Z Mihalić, H Vančik

Index: Simunic-Meznaric, Vesna; Mihalic, Zlatko; Vancik, Hrvoj Journal of the Chemical Society. Perkin Transactions 2, 2002 , # 12 p. 2154 - 2158

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Citation Number: 6

Abstract

Rearrangements of oximes in reactions with strong Lewis acids may include Beckmann alkyl group shift or hydride migration. These reaction mechanisms were studied by FT-IR spectroscopy in solid superacid cryogenic matrices and supported by ab initio calculations. It was found that cyclic oximes with smaller rings (cyclobutanone oxime and cyclopentanone oxime) undergo hydride migration rather than alkyl group shift. Resulting aminoallyl ...