Photo-Fries rearrangement of aryl acetamides: regioselectivity induced by the aqueous micellar green environment

IGUCHI DANIELA; ERRA-BALSELLS ROSA; BONESI SERGIO M.

Photochemical and Photobiological Sciences

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2015 vol. 15 p. 105 - 116

1474-905X

Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be apowerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a singlephotoproduct. Water?surfactant solutions as reaction media can be considered as an approach in thiscontext because they show products with different features than those from isotropic solutions. Here wedescribe results obtained from studying the effect on the prototypical photoreaction, known as thephoto-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactantmicelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C?N bond to yielda singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radicalpair, resulting in noticeable photoproduct selectivity.