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

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,...

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Veröffentlicht in:Journal of organic chemistry 2017-07, Vol.82 (14), p.7564-7575
Hauptverfasser: Savva, Anastasia C, Mirallai, Styliana I, Zissimou, Georgia A, Berezin, Andrey A, Demetriades, Marina, Kourtellaris, Andreas, Constantinides, Christos P, Nicolaides, Constantinos, Trypiniotis, Theodossis, Koutentis, Panayiotis A
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01297