Fred Capretta: Research Interests

Intramolecular Carbenoid Insertions in 5-Membered Aromatic Systems 

A number of examples exist in the chemical literature describing intramolecular carbenoid insertions into 5-membered aromatic systems. The outcome of these reactions is dependent not only on the nature of "X" (see below) but also on the length of the tether linking the diazoketone moiety with the aromatic fragment. We are presently studying novel diazo-systems (shown below) in an effort to develop facile synthetic routes to interesting heterocyclic systems. Concurrently, we are using molecular modelling to help explain the disparate chemistry seen for each system.

References: G. K. Tranmer and A. Capretta. Tetrahedron.1998, 54, 15499; K. Yong, M. Salim and A. Capretta. Journal of Organic Chemistry. 1998, 63, 9828-9833; C. S. Frampton, D.L. Pole, K. Yong and A. Capretta. Tetrahedron Letters. 1997, 38, 5081.