. alpha.-Oxygenation of aldehydes and cyclic ketones by acylation-rearrangement of nitrones
CH Cummins, RM Coates
Index: Cummins, Clark H.; Coates, Robert M. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2070 - 2076
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Citation Number: 59
Abstract
The reaction of N-tert-butylnitrones (la-e) of aldehydes and N-methylnitrones (2 and 3) of cyclic ketones with acid chlorides in the presence of triethylamine afforded a-acyloxy imines by rearrangement of N-vinyl-0-acylhydroxylamine intermediates. Hydrolysis of the a-acyloxy imines gave a-acyloxy aldehydes and ketones. The acylation-rearrangement reaction offers a new method for a-oxygenation of carbonyl compounds.
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