Selectivity in the Photo-Fries Rearrangement of Some Aryl Benzoates in Green and Sustainable Media. Preparative and Mechanistic Studies GastoĢn Siano Stefano Crespi Mariella Mella Sergio M. Bonesi 10.1021/acs.joc.9b00334.s001 https://acs.figshare.com/articles/journal_contribution/Selectivity_in_the_Photo-Fries_Rearrangement_of_Some_Aryl_Benzoates_in_Green_and_Sustainable_Media_Preparative_and_Mechanistic_Studies/7887440 Irradiation of a series of <i>p</i>-substituted aryl benzoates under N<sub>2</sub> atmosphere in homogeneous and micellar media was investigated by means of steady-state condition and of time-resolved spectroscopy. A notable selectivity in favor of the 2-hydroxybenzophenone derivatives was observed in micellar media. The benzophenone derivatives were the main photoproduct. On the other hand, in homogeneous media (cyclohexane, acetonitrile, and methanol) the observed product distribution was entirely different, viz. substituted 2-hydroxybenzophenones, <i>p</i>-substituted phenols, benzyl and benzoic acid were found. The binding constants in the surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of the micelle. Laser flash photolysis experiments led to the characterization of both <i>p</i>-substituted phenoxy radical and substituted 2-benzoylcyclohexadienone transients in homogeneous and micellar environment. 2019-03-15 00:00:00 2- benzoylcyclohexadienone transients N 2 atmosphere 2- hydroxybenzophenone derivatives NOESY micellar media aryl benzoates Mechanistic Studies Irradiation laser flash photolysis experiments