Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 9
245
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Chemical Oxidation Studies of β-Hydroxy-sulfides with tris(4-Bromophenyl)aminium Hexachloroantimonate: Diastereoselective Sulfoxide Obtaining and Pinacol-Type Rearrangement

, &
Pages 1489-1497 | Received 19 Jul 2001, Published online: 16 Aug 2006
 

Abstract

The chemical oxidation of some β-hydroxy-sulfides in the presence of tris(4-bromo-phenyl)aminium hexachloroantimonate (TBPA) is reported. The oxidation of 2-ethylsulfanyl-cyclohexan-l-ol (cis- and trans-) resulted the corresponding sulfoxides with good diastereoselectivity (d.e. ≈50%) and for 2-methyl-2-ethylsulfanyl-cyclohexan-l-ol and 2-ethylsulfanyl-1,2-diphenyl-ethanol, the corresponding non-sulfanylated ketones (61–75%) and ethyl ethanethiolsulfonate (51–65%) were obtained via oxidative cleavage and pinacol-type rearrangement.

Acknowledgments

The authors wish to thank Pró-Reitoria de Pesquisa (PRPQ/UFMG), Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), Programa de Apoio Desenvolvimento Cientifico e Tecnológico (PADCT), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.