Dan Lehnherr - Formal intramolecular photoredox chemistry of meta-substituted benzophenones

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  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