Influence of an Internal Trifluoromethyl Group on the Rhodium(II)-Catalyzed Reactions of Vinyldiazocarbonyl Compounds

Incorporation of a trifluoromethyl group into the structure of 4-(alkoxycarbonyl)vinyldiazocarbonyl compounds greatly decreases the tendency of the carbenoid intermediates formed during Rh(II)-catalyzed reactions to undergo intermolecular processes. Instead, they are prone to experience intramolecul...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-05, Vol.78 (9), p.4239-4244
Main Authors: Nikolaev, Valerij A, Supurgibekov, Murat B, Davies, Huw M. L, Sieler, Joachim, Zakharova, Valerija M
Format: Article
Language:English
Subjects:
Azo Compounds - chemistry
Catalysis
Chlorofluorocarbons, Methane - chemistry
Crystallography, X-Ray
Cyclization
Magnetic Resonance Spectroscopy
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Vinyl Compounds - chemistry
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Summary:Incorporation of a trifluoromethyl group into the structure of 4-(alkoxycarbonyl)vinyldiazocarbonyl compounds greatly decreases the tendency of the carbenoid intermediates formed during Rh(II)-catalyzed reactions to undergo intermolecular processes. Instead, they are prone to experience intramolecular [1,5]- and [1,3]-electrocyclizations to produce reactive cyclopropenes and furans, and these are capable of further transformations.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302726m