Electrooxidative coupling of salts of nitro compounds with halide,nitrite, cyanide,and phenylsulfinate anions |
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Authors: | A. I. Ilovaisky V. M. Merkulova Yu. N. Ogibin G. I. Nikishin |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | 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. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1539–1546, July, 2005. |
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Keywords: | nitroethane 1- and 2-nitropropanes nitrocyclohexane nitrocycloheptane halides nitrites cyanides phenylsulfinates electrolysis electrooxidative coupling gem-nitrohalides gem-dinitro compounds gem-nitronitriles gem-nitrosulfones |
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