Cathodic Cleavage of 1-Trifluoromethyl 1-Alkenyl Sulfone and Sulfoxide
The electrolytic desulfurization of organosulfur compounds has received considerable attention because most of them are valuable synthetic precursors. The previous paper showed that α,β-unsaturated α-fluoro sulfones such as 2-aryl-1-fluorovinyl phenyl sulfones were subjected to cleavage of carbon-sulfur and/or carbon-fluorine bonds to give 2-aryl-1-fluoro-ethylenes and arylethylenes with a molar ratio of about 1:1, in the presence of efficient proton donors such as phenol, acetic acid, and benzoic acid . On the other hand, the electrolytic reduction of α,β-unsaturated α-fluoro sulfoxide such as 2-(4-biphenylyl)-1-fluorovinyl phenyl sulfoxide involves desulfinylation, defluorination followed by reduction of the sulfinyl group, and reduction to the corresponding sulfide, resulting in the formation of 2-(4-biphenylyl)-1-fluoroethylene, 2-(4-biphenylyl)vinyl phenyl sulfide, and 2-(4-biphenylyl)-1-fluorovinyl phenyl sulfide, respectively .
KeywordsBenzoic Acid Acetic Anhydride Organosulfur Compound Single Electron Transfer Electrolytic Reduction
References and notes
- 3).In the case of 2-(4-biphenylyl)- I-fluorovinyl phenyl sulfoxide, the carboxylated product, 3-(4-biphenylyl)-2-fluoropropenoic acid was produced. See ref 2.Google Scholar