Nucleophilic Substitution on S4N4. Reactions with Benzylamines

Abstract

Reactions of benzylamines with tetrasulfur tetranitride lead to benzylidenimine polysulfides, ammonia, N-benzylidene benzylamines, and some free sulfur. The stoichiometric equation has been established. The reaction is quite sensitive to structural changes and appears limited to ring substituted benzylamines. The benzylidenimine polysulfides undergo thermal decomposition to sulfur and triphenyl-s-triazine and react with benzylamine to give benzylammonium polysulfides, ammonia, and N-benzylidene benzylamine. The benzylammonium polysulfides decompose in air to sulfur, hydrogen sulfide, and benzylammonium thiosulfate.