Photochemistry of charge-transfer complexes of tetracyanoethylene and tetracyanoquinodimethane with aliphatic nitriles

Upon irradiation, tetracyanoethylene (TCNE) in acetonitrile gave 2-amino-1,1-dicyanopropene, while tetracyanoquinodimethane (TCNQ) in isobutyronitrile gave 1-(4-dicyanomethylphenyl)-2-methylpropane-1,1,2-tricarbonitrile; mechanisms involving electron transfer in which liphatic nitriles behave as electron donors are proposed.