Journal of Organic Chemistry p. 2070 - 2076 (1983)
Update date:2022-07-29
Topics:
Cummins, Clark H.
Coates, Robert M.
The reaction of N-tert-butylnitrones (1a-e) of aldehydes and N-methylnitrones (2 and 3) of cyclic ketones with acid chlorides in the presence of triethylamine afforded α-acyloxy imines by rearrangement of N-vinyl-O-acylhydroxylamine intermediates.Hydrolysis of the α-acyloxy imines gave α-acyloxy aldehydes and ketones.The acylation-rearrangement reaction offers a new method for α-oxygenation of carbonyl compounds.
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(1941)Doi:10.1016/S0040-4039(00)85635-X
(1982)Doi:10.1002/hlca.19480310509
(1948)Doi:10.1021/jo00161a005
(1983)
