Electrochlorination of diphenylsulfide and diphenyloxide with methylene chloride

Abstract

The electrochlorination of diphenylsulfide and diphenyloxide was carried out in an undivided cell with C rod electrode, using tetraethylammonium p-toluenesulfonate or chloride as supporting electrolyte and methylene chloride as solvent. 4,4'-Dichlorodiphenylsulfide, 4-chlorodiphenylsulfide and the corresponding oxides were obtained, resp. Triphenylphosphine could not be chlorinated under this condition. The test of electrolytic condition and cyclovoltammogram showed that the chloronium ion generated from the electrolysis of methylene chloride was the chlorinating agent.

Key words: DICHLOROMETHANE, SUBSTITUTION REACTION, SULFUR ETHER, CHLORINATION REACTION, PHENYL ETHER, ELECTROCHEMICAL REACTION, ELECTROPHILIC REACTION

CLC Number:

O621

Cite this article

WANG ZHIQIN;ZHOU WENJUAN. Electrochlorination of diphenylsulfide and diphenyloxide with methylene chloride[J]. Chin. J. Org. Chem., 1988, 8(5): 462-465.

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