Regularities of anodic acetoxylation of 1,4-dimethoxybenzene in protic and aprotic media |
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Authors: | V A Petrosyan T S Vakhotina A V Burasov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Electrochemical acetoxylation of 1,4-dimethoxybenzene during amperostatic electrolysis in an undivided cell at Pt electrodes
in MeCN or MeOH solutions containing Et4NOAc gives 2,5-dimethoxyphenyl acetate if AcOH or CH2Cl2 co-solvent has been added in a concentration of ≥50%. The reaction mechanism includes a nucleophilic attack of AcO− ion on the ipso-position of 1,4-dimethoxybenzene radical cation. The process efficiency depends on factors that determine the stability and
reactivity of the intermediate 1,4-dimethoxy-1-acetoxyarenonium cation.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1534–1538, July, 2005. |
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Keywords: | anodic acetoxylation 1 4-dimethoxybenzene tetraethylammonium acetate 1 4-dimethoxy-1-acetoxyarenonium cation 2 5-dimethoxyphenyl acetate |
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