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Preparation of Blatter radicals via aza-Wittig chemistry: The reaction of N-aryliminophosphoranes with 1-(het)aroyl-2-aryldiazenes

Savva, Anastasia C., Mirallai, Styliana I., Zissimou, Georgia A., Berezin, Andrey A., Demetriades, Marina, Kourtellaris, Andreas, Constantinides, Christos P., Nicolaides, Constantinos, Trypiniotis, Theodossis and Koutentis, Panayiotis 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) , pp. 7564-7575. 10.1021/acs.joc.7b01297

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 24 Jan 2020 13:30
URI: http://orca-mwe.cf.ac.uk/id/eprint/128752

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