Download PDF
Synthesis 1994; 1994(4): 401-404
DOI: 10.1055/s-1994-25486
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Facile Oxidation of Sulfides to Sulfoxides using Sodium Hypochlorite and Oxoammonium Salt as a Catalyst: Chemo- and Diastereoselective Transformation of Bis(phenylthio)alkanes into Sulfoxides

Renata Siedlecka* , Jacek Skarżewski
  • *Institute of Organic Chemistry, Biochemistry and Biotechnology, Technical University, PL-50-370 Wrocław, Poland
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A facile and selective method for the title transformation is described. The two-phase oxidation of disulfides with one or two equivalents of sodium hypochlorite mediated by TEMPO and co-catalyzed by potassium bromide and PTC leads to the corresponding mono- or disulfoxides, respectively. In the case of 1,2- 1,3-bis(phenylthio)alkanes and ortho-bis(phenylthiomethyl)benzene the respective meso disulfoxides are formed in 90-98% diastereoselectivity.