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

DANIELA IGUCHI; ERRA BALSELLS ROSA; BONESI SERGIO M

Photochemical and Photobiological Sciences

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2016 vol. 15 p. 105 - 116

1474-905X

Abstract. Photochemical reactions tend to give more than one photoproduct. However, such reactions can be a powerful synthetic tool when is possible to conduct it in regioselective conditions yielding a single photoproduct. Water ? surfactant solutions as reaction media can be considered as an approach in this context because show products feature different than those from isotropic solutions. Here we describe results obtained studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and -naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C ? N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.