title: "Ene" Reactions of Singlet Oxygen at the Air-Water Interface.
abstract: Prenylsurfactants [(CH3)2C═CH(CH2)nSO3(-) Na(+) (n = 4, 6, or 8)] were designed to probe the "ene" reaction mechanism of singlet oxygen at the air-water interface. Increasing the number of carbon atoms in the hydrophobic chain caused an increase in the regioselectivity for a secondary rather than tertiary surfactant hydroperoxide, arguing for an orthogonal alkene on water. The use of water, deuterium oxide, and H2O/D2O mixtures helped to distinguish mechanistic alternatives to homogeneous solution conditions that include dewetting of the π bond and an unsymmetrical perepoxide transition state in the hydroperoxide-forming step. The prenylsurfactants and a photoreactor technique allowed a certain degree of interfacial control of the hydroperoxidation reaction on a liquid support, where the oxidant (airborne (1)O2) is delivered as a gas.
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.
authors.forename: Belaid
authors.initials: B
authors.lastname: Malek
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.
authors.forename: William
authors.initials: W
authors.lastname: Fang
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.
authors.forename: Inna
authors.initials: I
authors.lastname: Abramova
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.|Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , 365 Fifth Avenue, New York, New York 10016, United States.
authors.forename: Niluksha
authors.initials: N
authors.lastname: Walalawela
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.|Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , 365 Fifth Avenue, New York, New York 10016, United States.
authors.forename: Ashwini A
authors.initials: AA
authors.lastname: Ghogare
authors.affiliation: Department of Chemistry, Brooklyn College of the City University of New York , Brooklyn, New York 11210, United States.|Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , 365 Fifth Avenue, New York, New York 10016, United States.
authors.forename: Alexander
authors.initials: A
authors.lastname: Greer