Publication Details (including relevant citation information):
D. Mitchell, M. Lukeman, D. Lehnherr, P. Wan. Organic Letters 2005, 7, 3387-3389
Photolysis of 3-(hydroxymethyl)benzophenone (1) in aqueous solution (pH < 3) results in clean formation of 3-formylbenzhydrol (2) at dilute (<10-4 M) conditions. Evidence suggests that the highly efficient (Φ 0.6) reaction involves a unimolecular mechanism and an overall formal intramolecular photoredox process, which requires electronic communication between the 1,3-positions of the benzene ring, an unprecedented example of the photochemical meta effect. The photoredox reaction was not observed in organic solvents, where only photoreduction of the benzophenone moiety was observed.
Address (URL): http://pubs.acs.org/doi/abs/10.1021/ol051381u