One-Pot Synthesis and Asymmetric Oxidation of 2-Nitro-4-(Trifluoromethyl)Benzene Containing Sulfides |
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| Authors: | Konstantin S Rodygin Svetlana A Rubtsova Alexander V Kutchin Pavel A Slepukhin |
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| Institution: | Institute of Chemistry of Komi Scientific Centre, Ural Branch of Russian Academy of Sciences , Syktyvkar, Russia |
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| Abstract: | Abstract An efficient one-pot method for the preparation of 2-nitro-4-(trifluoromethyl)benzene containing sulfides from 1,1′-disulfanediylbis2-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  |
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| Keywords: | Fluorinated sulfides fluorinated sulfoxides asymmetric sulfoxidation Sharpless method |
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