title: The power of solvent in altering the course of photorearrangements.
abstract: A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (~8%). The surprisingly clean yields suggest that such reactions are synthetically promising.
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00, Brno, Czech Republic.
authors.forename: Peter
authors.initials: P
authors.lastname: Šebej
authors.forename: Bum Hee
authors.initials: BH
authors.lastname: Lim
authors.forename: Bong Ser
authors.initials: BS
authors.lastname: Park
authors.forename: Richard S
authors.initials: RS
authors.lastname: Givens
authors.forename: Petr
authors.initials: P
authors.lastname: Klán
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D055668:Photochemical Processes; D012997:Solvents; D014867:Water / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D001572:Benzofurans; D004952:Esters; D007189:Indans; D012997:Solvents; D014867:Water