Regioselective aerobic oxidation of bis-sulfides into monosulfoxides

Authors
Dell'Anna, MM Mastrorilli, P Nobile, CF Taurino, MR Calo, V Nacci, A
Citation
Mm. Dell'Anna et al., Regioselective aerobic oxidation of bis-sulfides into monosulfoxides, J MOL CAT A, 151(1-2), 2000, pp. 61-69
Citations number
20
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
ISSN journal
13811169 → ACNP
Volume
151
Issue
1-2
Year of publication
2000
Pages
61 - 69
Database
ISI
SICI code
1381-1169(20000215)151:1-2<61:RAOOBI>2.0.ZU;2-P
Abstract
The cobalt(II) acetylacetonate/aldehyde-promoted aerobic oxidation of three bis-sulfides of general formula R-1-SCH2CH2S-R-2, where R-1 is a heterocyc le and R-2 is p-tolyl, provides a method to functionalise selectively the s ulfur atom bonded to the p-tolyl moiety leading to the corresponding monosu lfoxides. The same chemoselectivity and Little diastereoisomeric excess (10 %) was achieved by submitting to oxidative conditions the chiral bis-sulfid e (S)-R-3- SCH2CH(CH3)CH2-SR4 (R-3 = benzothiazolyl, R-4 = p-tolyl). (C) 20 00 Elsevier Science B.V. All rights reserved.