Unexpected reductive double carbon–carbon bonds cleavage of bicyclic nitrocyclopropanes

Reductive treatment of bicyclic nitrocyclopropanes with zinc powder under acidic conditions resulted in the double cleavage of carbon–carbon bonds in the cyclopropane to give vinyl nitrile in good yields. The reductive cleavage of carbon–carbon bond depended on the reaction conditions and sufficient acidic treatment gave alkenyl nitriles in good yields, while weak acidic treatment afforded oxime derivative instead.