Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes
Panayiotis A. Koutentis, Christos P. Constantinides, Marina Demetriades, Georgia A. Zissimou, Theodossis Trypiniotis, Andreas Kourtellaris, Andrey A. Berezin, Styliana I. Mirallai, Anastasia C. Savva, Constantinos Nicolaides
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01297

DOI: 10.1021/acs.joc.7b01297

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