Mechanism of the oxidation of sulfides by dioxiranes: conformational mobility and transannular interaction in the oxidation of thianthrene 5-oxide |
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| Authors: | González-Núñez María Elena Mello Rossella Royo Jorge Asensio Gregorio Monzó Isidro Tomás Francisco López Jesús García Ortiz Fernando López |
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| Institution: | Departamento de Química Orgánica, Universidad de Valencia, Avda. V. Andrés Estellés s/n, 46100-Burjassot (Valencia), Spain. |
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| 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. |
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