Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions

Article abstract of DOI:10.1007/s11172-006-0007-7

Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH₂Cl₂/H₂O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.