title: Mechanism of the oxidation of sulfides by dioxiranes: conformational mobility and transannular interaction in the oxidation of thianthrene 5-oxide.
abstract: The detailed study of the oxidation of thianthrene 5-oxide (1) with methyl(trifluoromethyl)dioxirane (5b) in different solvents and in the presence of (18)O isotopic tracers is reported. Thianthrene 5-oxide (1) is a flexible molecule in solution, and this property allows for transannular interaction of the sulfoxide group with the expected zwitterionic 7 and hypervalent 10-S-4 sulfurane 9 intermediates formed in the oxidation and biases the course of the reaction toward the monooxygenation pathway.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, Avda. V. Andrés Estellés s/n, 46100-Burjassot (Valencia), Spain.
authors.forename: María Elena
authors.initials: ME
authors.lastname: González-Núñez
authors.forename: Rossella
authors.initials: R
authors.lastname: Mello
authors.forename: Jorge
authors.initials: J
authors.lastname: Royo
authors.forename: Gregorio
authors.initials: G
authors.lastname: Asensio
authors.forename: Isidro
authors.initials: I
authors.lastname: Monzó
authors.forename: Francisco
authors.initials: F
authors.lastname: Tomás
authors.forename: Jesús García
authors.initials: JG
authors.lastname: López
authors.forename: Fernando López
authors.initials: FL
authors.lastname: Ortiz