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 (Kb) and the location of the esters within the hydrophobic core of the spherical micelles. Furthermore, the diffusion coefficient (D) and hydrodynamic radius (rs) 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.