K. Rodygin, S. A. Rubtsova, A. Kutchin
Aug 24, 2011
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Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Abstract An efficient one-pot method for the preparation of 2-nitro-4-(trifluoromethyl)benzene containing sulfides from 1,1′-disulfanediylbis[2-nitro-4-(trifluoromethyl)benzene] is proposed. The corresponding enantiomerically enriched sulfoxides with up to 78% enantiomeric excess are prepared by the asymmetric oxidation of sulfides using a modified Sharpless method. The yield of sulfoxides is shown to decrease with an increase in the bulk of the aliphatic group and with a decrease of the inductive effect of the hydrocarbonic moiety on the sulfur atom. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT