Radical cyclization/fragmentation reactions of dicyanocyclopropanes to enaminonitriles. A radical alternative to the Thorpe-Ziegler reaction

Radical cyclizations to dicyanocyclopropanes provide cyclic enaminonitriles by a series of radical reactions that features radical cyclization to a ni trile and cyclopropane cleavage. The direction of cyclopropane cleavage-and hence the ring size of the final product-depends on the nature of the ring formed in the initial cyclization to the nitrile.