title: Stereochemistry of the singlet oxygenation of simple alkenes: a stereospecific transformation.
abstract: The stereochemistry of the allylic oxidation (ene reaction) mediated by singlet oxygen ((1)O2), using the optically active alkene (S,S)-cis-1,4-diphenyl-2-butene-1,4-d2 , in MeOH and aprotic solvents was investigated. Our findings indicate that the title reaction is a highly stereospecific suprafacial process, independent of solvent polarity. The observation of an isotope effect, which matches the stereogenic ratio exactly, rules out biradical or open dipolar intermediates.
authors.affiliation: Department of Chemistry, University of Crete, 71003, Voutes-Heraklion, Crete, Greece.
authors.forename: Mariza N
authors.initials: MN
authors.lastname: Alberti
authors.forename: Georgios
authors.initials: G
authors.lastname: Vassilikogiannakis
authors.forename: Michael
authors.initials: M
authors.lastname: Orfanopoulos