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.