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

Authors: Valerij A. Nikolaev , Murat B. Supurgibekov , Huw M. L. Davies , Joachim Sieler , and Valerija M. Zakharova

J. Org. Chem.,

2013, 78 (9), 4239–4244


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.

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