Evidence for nitrene formation via pyrolysis of an NN-dihalogenoaniline: thermal conversion of NN-dichloroperfluoro-p-toluidine into perfluoro-(2-dichloromethyl-4-methylpyridine) and perfluoro-(1-cyano-4-methylcyclopenta-1,3-diene)

Abstract

Flow pyrolysis of NN-dichloroperfluoro-p-toluidine at 550 °C and ca. 1 mmHg yields, inter alia, perfluoro-4,4′-azotoluene, perfluoro-4-chlorotoluene, perfluoro-(2-dichloromethyl-4-methylpyridine) and perfluoro-(1-cyano-4-methylcyclopenta-1,3-diene); formation of the last two compounds suggests that perfluoro-p-tolylinitrene is implicated.