Decompositions of α, α'-Azobisisobutyronitrile in Various Aromatic Compounds

1-Cyano-l-methylethyl radicals produced by the decomposition of α, α'-azobisisobutyronitrile attacked dimethylaniline yielding 2, 4-bis-(1-cyano-1-methyl ethyl)-dimethylaniline. 1-Cyano-1-methylethyl radicals, however, did not react with aniline, diethylaniline, acetanilide, pyridine, anisole, acetophenone, benzonitrile, azobenzene, and benzoin. The reaction mechanism is discussed in terms of electron transfer. a, N-Diphenylnitrone combined with two 1-cyano-1-methylethyl radicals to produce N-phenyl-N-[α-(1-cyano-1-methylethyl)-benzy1]-O-(1- cyano-1-methylethyl)-hydroxylamine in 63% yield. This reaction is a new type of addition. 1-Cyano-1-methylethyl radicals did not add to a C=N bond.