title: Exploring the Photophysical and Photochemical Properties of N-(Thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams.
abstract: Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom.
authors.affiliation: INFIQC-CONICET-UNC, Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria , X5000HUA Córdoba, Argentina.
authors.forename: Willber D
authors.initials: WD
authors.lastname: Castro-Godoy
authors.affiliation: INFIQC-CONICET-UNC, Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria , X5000HUA Córdoba, Argentina.
authors.forename: Gabriela
authors.identifier: 0000-0002-8999-3314
authors.initials: G
authors.lastname: Oksdath-Mansilla
authors.affiliation: INFIQC-CONICET-UNC, Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria , X5000HUA Córdoba, Argentina.
authors.forename: Juan E
authors.initials: JE
authors.lastname: Argüello
authors.affiliation: INFIQC-CONICET-UNC, Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria , X5000HUA Córdoba, Argentina.
authors.forename: Alicia B
authors.initials: AB
authors.lastname: Peñéñory