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

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.