Abstract
The properties of 4-methyl-4-(trichloromethyl)cyclohexa-2,5-dien-1-one which contains the trichloromethyl substituent at a quaternary carbon atom have been studied by cyclic voltammetry, rotating disk electrode voltammetry, and preparative electrolysis. Reductive dehalogenation involves initial two-electron reductive elimination of one of the geminal chlorine atoms followed by consecutive addition of proton, simultaneous elimination of the two residual halogen atoms to form carbene, and rearrangement of cyclohexadienone into the corresponding 4-methylcyclohepta-2,4,6-trien-1-one.
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Original Russian Text © A.A. Moiseeva, G.V. Gavrilova, L.N. Vykhodtseva, S.N. Nikolaeva, D.P. Krut’ko, E.K. Beloglazkina, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 6, pp. 890–895.
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Moiseeva, A.A., Gavrilova, G.V., Vykhodtseva, L.N. et al. Electrochemical reduction of 4-methyl-4-(trichloromethyl)cyclohexa-2,5-dien-1-one. Russ J Gen Chem 84, 1074–1078 (2014). https://doi.org/10.1134/S1070363214060036
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DOI: https://doi.org/10.1134/S1070363214060036