Issue 1, 2016

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

Abstract

Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it 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 they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-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.

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2015
Accepted
24 Nov 2015
First published
01 Dec 2015

Photochem. Photobiol. Sci., 2016,15, 105-116

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

D. Iguchi, R. Erra-Balsells and S. M. Bonesi, Photochem. Photobiol. Sci., 2016, 15, 105 DOI: 10.1039/C5PP00349K

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