Mechanism of the oxidation of sulfides by dioxiranes: conformational mobility and transannular interaction in the oxidation of thianthrene 5-oxide.

6533b85ffe1ef96bd12c13a4

RESEARCH PRODUCT

Mechanism of the oxidation of sulfides by dioxiranes: conformational mobility and transannular interaction in the oxidation of thianthrene 5-oxide.

María Elena González Núñez Isidro S. Monzó Jorge Royo Rossella Mello Fernando López Ortiz Jesús García López Gregorio Asensio Francisco Tomás

subject

chemistry.chemical_compound Reaction mechanism Trifluoromethyl chemistry Dioxirane Zwitterion Organic Chemistry Hypervalent molecule Sulfoxide Solvent effects Photochemistry Thianthrene

description

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.

year	journal	country	edition	language
2004-12-22	The Journal of organic chemistry

10.1021/jo0483062 https://pubmed.ncbi.nlm.nih.gov/15609942

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