A facile dehomologation of α-substituted aldehydes to the corresponding ketones

Article abstract of DOI:10.1016/0040-4039(95)00467-Q

A systematic study has been completed demonstrating the utility and scope of the potassium dichromate-mediated oxidative cleavage of enamines. Among the methods studied, the biphasic, chromic acid-diethyl ether conditions gave the best results and prevented over-oxidation of the carbonyl products. This method is general for β,β-disubstituted enamines, such as (1E)-1-(4-morpholino)-2-phenyl-2-methyl-1-propene, and gave the corresponding dehomologated ketones in good yield in one hour at 25°C.