Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes

Abstract

Reacting N-aryliminophosphoranes with 1-(het)aroyl-2-aryldiazenes in preheated diphenyl ether at ca. 150-250 °C for 5-25 min affords in most cases the 1,3-diaryl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yls (aka Blatter radicals) in moderate to good yields. All new compounds are fully characterized, including EPR and CV studies for the radicals. Single-crystal X-ray structures of 1-benzoyl-2-(perfluorophenyl)diazene and 1-(perfluorophenyl)-3-phenyl-1,4-dihydrobenzo[e][1,2,4]triazinyl are also presented. © 2017 American Chemical Society.