Abstract

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 C N bond and the ring expansion reaction of the azirine moiety affording the four-membered ring intermediate 2•+.

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