Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes
Date
2017Author
Savva, Anastasia C.Mirallai, Styliana I.
Zissimou, Georgia A.
Berezin, Andrey A.
Demetriades, Marina
Kourtellaris, Andreas
Constantinides, Christos P.
Nicolaides, C.
Trypiniotis, Theodossis
Koutentis, Panayiotis Andreas
Source
Journal of Organic ChemistryVolume
82Issue
14Pages
7564-7575Google Scholar check
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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.