Thermolysis of mono-, di- and tri-benzylamines, IV

Thermolysis of mono-, di- or tri-benzylamine for some days in the absence of promoters gave the same products: ammonia, toluene, dibenzyl, stilbene and benzaldehyde. Thermolysis of dibenzylamine in isoquinoline as a solvent gave 1-benzyl-isoquinoline together with the normal pyrolysis products. When naphthalene and 2-naphthol are used as solvents, benzylation of the solvent nuclei was observed to give 1- and 2-benzylnaphthalenes and 1-benzyl-2-naphthol respectively. In conclusion, thermolysis of tri-, di- or mono-benzylamines proceeds through a free radical mechanism with successive conversions of the tertiary, through secondary to primary alkylamines resulting in the same pyrolysis products.