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- W1963603079 abstract "Oxidation of the 2-phosphino-2H-azirine 1 by preparative scale electrolysis quantitatively leads to the four-membered phosphonium heterocycle 3, while addition of tetrachloro-o-benzoquinone to 1 produces an eight-membered heterocycle 4 with 60 % yield. In both cases, the first step is the formation of a transient phosphorus centered radical cation 1•+, which induces the cleavage of the CN bond and the ring expansion reaction of the azirine moiety affording the four-membered ring intermediate 2•+. Réactions d'extension de cycle lors de l'oxydation d'une 2-phosphino-2H-azirine. L'oxydation par voie électrochimique de la 2-phosphino-2H-azirine 1 conduit quantitativement au sel de phosphonium cyclique à quatre chaînons 3, alors que l'addition de la tétrachloro-o-benzoquinone sur 1 permet l'obtention de l'hétérocycle à huit chaînons 4, isolé avec un rendement de 60 %. Dans les deux cas, il y a formation transitoire dans une première étape d'un radical cation centro-phosphoré 1•+ qui induit une réaction d'extension du cycle azirine, mettant en jeu la rupture de la liaison CN, et conduisant à l'intermédiaire cyclique à quatre chaînons 2•+." @default.
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- W1963603079 date "1998-02-01" @default.
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- W1963603079 title "Oxidation-induced ring expansion of a 2-phosphino-2H-azirine" @default.
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- W1963603079 doi "https://doi.org/10.1016/s1251-8069(97)86271-9" @default.
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