Pyrolysis of 1,2-diphenylethylamine and related amines

When 1,2-diphenylethylamine is pyrolyzed at 300°, the major products are ammonia, 1,2-diphenylethane, stilbene, J desoxybenzoin, and tetraphenylpyrrole. Preliminary experiments with alpha-phenylethylamine, 2,2-diphenylethylamine, n-hexadecylamine, and diphenylmethylamine indicate similar results. When N, N-dimethylamines attached to primary J carbons are heated, an alkane and 1,3,5-trimethylhexahydros-triazine are formed. Primary amines attached to tertiary carbons do not appear to react at 300° whereas their N,N-dimethyl derivatives yield alkanes and the previously mentioned triazine.