Azomethine Imines in Four- and Five-Membered Rings: Stable Cyclic Valence Isomers of an α-(Phenyldiazenyl)ketocarbene

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 cy...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 1998-09, Vol.37 (16), p.2229-2231
Main Authors: Schantl, Joachim G., Rettenbacher, Arno S., Wurst, Klaus
Format: Article
Language:English
Subjects:
Azo compounds
Carbenes
Imines
Isomerizations
Rearrangements
Online Access:Get full text
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19980904)37:16<2229::AID-ANIE2229>3.0.CO;2-#