Reactions of Enamines with Dehydro Aromatic Compounds

Article abstract of DOI:10.1021/jo00040a016

Benzyne reacts with enamines through a combination of ene and 2 + 2 cycloadditions.One of the two possible ene reactions is greatly favored.The three-dimensional intermediate, 1,2-dehydro-o-carborane, eschews the 2 + 2 reaction in favor of the ene reaction that is less favored in the benzyne reactions.This preference is rationalized in terms of the different steric demands of the two intermediates.