Abstract
The expected Wolff rearrangement of the ketocarbene intermediate 2, formed upon rhodium(II)-catalyzed elimination of nitrogen from diazoketone 1, does not occur. Instead, by incorporation of the neighboring diazene group the surprisingly stable, crystalline azomethine imines 3 and 4 are formed as cyclic valence isomers of 2. Compound 4, which contains a five-membered ring, is the first representative of a carba-sydnone and can also be obtained by acid-catalyzed isomerization of 3 at 50-70°C.
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