Electrochemical <Emphasis Type="Italic">N</Emphasis>-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene |
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Authors: | V A Petrosyan A V Burasov T S Vakhotina |
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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: | The reactions of 1,4-dimethoxybenzene with azoles (pyrazole, triazole, and their derivatives, as well as tetrazole) were studied
by undivided amperostatic electrolysis at Pt electrodes in MeOH. The process proceeds via the formation of a 1,1,4-trimethoxyarenonium cation as the key intermediate and affords 1,1,4,4-tetramethoxycyclohexa-2,5-diene,
1,1,4-trimethoxy-4-(azol-1-yl)cyclohexa-2,5-diene, and 1,4-dimethoxy-2-(azol-1-yl)benzene as the main products. Azole and
solvent molecules compete as nucleophiles during electrolysis. A fine mechanism of the process was considered.
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1166–1171, May, 2005. |
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Keywords: | azoles 1 4-dimethoxybenzene paired electrosynthesis N-dimethoxyphenylazoles |
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