EVIDENCE FOR THE INVOLVEMENT OF A SULFURANE INTERMEDIATE IN THE OXIDATION OF SIMPLE SULFIDES BY METHYL(TRIFLUOROMETHYL)DIOXIRANE

Authors
ASENSIO G MELLO R GONZALEZNUNEZ ME
Citation
G. Asensio et al., EVIDENCE FOR THE INVOLVEMENT OF A SULFURANE INTERMEDIATE IN THE OXIDATION OF SIMPLE SULFIDES BY METHYL(TRIFLUOROMETHYL)DIOXIRANE, Tetrahedron letters, 37(13), 1996, pp. 2299-2302
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
13
Year of publication
1996
Pages
2299 - 2302
Database
ISI
SICI code
0040-4039(1996)37:13<2299:EFTIOA>2.0.ZU;2-4
Abstract
Methyl(trifluoromethyl)dioxirane reacts with sulfides to give preferen tially sulfones, even in the presence of competing sulfoxides. The sul foxide yield increases at the expense of the sulfone when 2,2,2-triflu oroethanol is used as co-solvent. The reaction of dioxirane Ib with ph enylmethyl sulfide in the presence of 1,1,1-trifluoropropanone-O-18-hy drate (48% atom labelled), leads to the obtention of 23% atom O-18-lab elled sulfoxide and 6.1% atom O-18-labelled sulfone. The involvement o f a cyclic hypervalent sulfurane intermediate is proposed as reactive intermediate.