Nickel(0) - Catalyzed Reactions of Bicyclopentane and Electron-Deficient Olefins

Article abstract of DOI:10.1021/jo00327a003

In the presence of a catalytic amount of bis(acrylonitrile)nickel(0), bicyclo<2.1.0>pentane suffers from the cleavage of the central ? bond and cycloadds to electron-deficient olefins such as methyl acrylate, acrylonitrile, dimethyl maleate, and dimethyl fumarate to give bicyclo<2.2.1>heptane derivatives.The stereochemistry and mechanism of the catalyzed cycloadditions have been elucidated by use of deuterated bicyclo<2.1.0>pentanes.