On the Stereoselective Behavior in the Photochemical Paternò–Büchi Reaction of Benzophenone With Phenyl‐(2‐furyl)Methanol

ABSTRACT

Paternò–Büchi reaction between benzophenone and phenyl‐(2‐furyl)methanol gave the corresponding oxetane with high stereoselectivity. DFT calculations at B3LYP/aug‐cc‐pVDZ level of theory showed that triplet benzophenone and the hydroxy group on the furan derivative can interact through hydrogen bond formation. These adducts can be converted into the corresponding biradical intermediates and the reactions allowing the formation of R,R biradical intermediate are faster than those able to give R,S biradical intermediate, in agreement with the experimental results.