Effect of Confined and Micellar Media on the Photo-Fries Reaction of 4-Phenoxyphenol Esters: A Valuable Key Step Toward the Preparation of Aryloxyethyl Selenocyanates

Abstract

The irradiation of a series of 4-phenoxyphenol esters in a sustainable micellar environment has been studied from both preparative and mechanistic viewpoints, and the results were compared with those obtained in cyclohexane solutions. These esters underwent the photo-Fries rearrangement reaction, and the microheterogeneous media induced a noticeable selectivity in favor of the ortho-regioisomer formation with yields up to 96% yield. UV–visible and 1D and 2D NMR (DCS, NOESY, and DOSY) spectroscopies have been employed to determine the binding constant (K_b) and the location of the esters within the hydrophobic core of the spherical micelles. Furthermore, the diffusion coefficient (D) and hydrodynamic radius (r_s) were also measured. Application of the photo-Fries reaction of esters in microheterogeneous media as a key step in a multistep sequence has been carried out, leading to the preparation of (4-phenoxy)-(2-n-pentylcarbonyl)-phenoxyethyl selenocyanate (10), an interesting target molecule showing potential biological activity against Trypanosoma cruzi.