N-Phenacyloxycarbamates and other systems containing a CH,-0-N= framework, in the presence of bases, undergo a CH,-0-N= --+ CH(0H)-N= rearrangement. The mechanism of this reaction has been studied kinetically and through crossover and capture experiments. The bulk of the data favours an intermolecular ionic mechanism which occurs by removal of a proton from the methylene group in the rate-determining step, followed by interaction between a glyoxal molecule and a carbamate anion in the fast step of the reaction.* a-Chloro-a-phenylacetophenone.

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