Synthetic Reactions by Complex Catalysts. XXV. The Copper-catalyzed Reaction of Allyl Isocyanide with Carbonyl Compounds and Olefins. Syntheses of 4-Vinyl-2-oxazoline and 5-Vinyl-1-pyrroline Derivatives

This paper describes two reactions of allyl isocyanide (AIC) by means of the Cu2O catalyst; these reactions produce heterocyclic compounds with vinyl substituents. First, the reactions of AIC with such carbonyl compounds as ketones and aldehydes produce 4-vinyl-2-oxazoline derivatives (1) in good yields. Second, AIC also reacts with the C=C double bond of α,β-unsaturated nitriles and esters to produce 5-vinyl-1-pyrroline derivatives (4,5, and 6). A mechanistic scheme involving an isocyanoallylcopper complex (11) has been assumed.