Although synthetic chemists typically regard carbon-carbon single bonds as inert, they have used metal catalysts to spring open C–C bonds in strained rings, such as cyclopropanes and cyclobutanes. Performing a similar transformation with less strained but more common five- and six-membered rings, however, has proven more difficult.
Now, synthetic and theoretical chemists report a way of opening up C–C bonds in aryl substituted cyclopentanones to produce α-tetralones. The reaction was developed by University of Chicago’s Guangbin Dong and Ying Xia, and at Pitt, Peng Liu and his post doc Gang Lu studied the mechanism from a quantum chemical point of view with DFT (Density Functional Theory) calculations.
The results are published in the online issue of Nature.