Chemo- and stereo-selectivity in oxidation of fluorinated cyclic sulfides by m-chloroperoxybenzoic acid

• Chemoselective conversion of hexafluorothioacetone cycloadducts into sulfoxides.
• Stereoselective synthesis of cyclic fluorinated sulfoxides.
• Chemo- and regio-selective oxidation of 3,3-bis(trifluoromethyl)-1,2-dithiolane.

Controlled oxidation of various hexafluorothioacetone cycloadducts by m-chloroperoxybenzoic acid (MCPBA) at low temperature led to the formation of the corresponding cyclic sulfoxides in 56–82% yield. The oxidation of 5-ethoxy-3,3-bis(trifluoromethyl)-1,2-dithiolane proceeded selectively leading to trans-5-ethoxy-3,3-bis(trifluoromethyl)-1,2-dithiolane-1-oxide, which underwent selective isomerization into the cis-isomer at higher temperature.

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