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

Anastasia C. Savva, Styliana I. Mirallai, Georgia A. Zissimou, Andrey A. Berezin, Marina Demetriades, Andreas Kourtellaris, Christos P. Constantinides, Constantinos Nicolaides, Theodossis Trypiniotis, Panayiotis A. Koutentis

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30 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7564-7575
Number of pages12
JournalJournal of Organic Chemistry
Volume82
Issue number14
DOIs
Publication statusPublished - 21 Jul 2017

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    Savva, A. C., Mirallai, S. I., Zissimou, G. A., Berezin, A. A., Demetriades, M., Kourtellaris, A., Constantinides, C. P., Nicolaides, C., Trypiniotis, T., & Koutentis, P. A. (2017). Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes. Journal of Organic Chemistry, 82(14), 7564-7575. https://doi.org/10.1021/acs.joc.7b01297