Reaction of cyclohexanone enamines with diacyldi-imides
Abstract
Cyclohexanone morpholine and piperidine-enamines react with diacyldi-imides to give only monocycloaddition products, while pyrrolidine enamines also give bisaddition products in the 2,2- and 2,6-positions. The results of hydrolysis in D2O form the basis of a reaction scheme which takes the experimental findings into account. Dibenzoyldi-imide reacts with 2-methylcyclohexanone enamines giving two stereoisomeric cycloadducts, which are different in the orientatation of the methyl group, while bisaddition products could not be isolated. The stereochemistry of the reaction is discussed.