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

C Luis Donnici, S Guimarães…

Index: Donnici, Claudio Luis; Guimaraes, Sibele; De Melo, Angelita Cristine Synthetic Communications, 2003 , vol. 33, # 9 p. 1489 - 1497

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Abstract

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 (de≈ 50%) and for 2-methyl-2-ethylsulfanyl-cyclohexan-l-ol and 2- ethylsulfanyl-1, 2-diphenyl-ethanol, the corresponding non-sulfanylated ketones (61–75% ...