Work

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

Year: 2025

Type: article

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 .

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c02969

Authors: Valentín Lucena, Juan B. Rodriguez, Sergio H. Szajnman, Sergio M. Bonesi

Institutions: Consejo Nacional de Investigaciones Científicas y Técnicas, Universidad de Buenos Aires

Language: English

Topic: Surfactants and Colloidal Systems

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Universidad de Buenos Aires, Agencia Nacional de Promoción Científica y Tecnológica

Awards: G3754870414, G3857138858, G8118123592