- Electrochemically induced oxidative rearrangement of alkylidenemalonates
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Alkylidenemalonates capable of double bond migration being electrolyzed in methanol or ethanol in the presence of alkali metal halides in an undivided cell equipped with Fe cathode are transformed into 2-alkyl-3,3- dimethoxyalkane-1,2-dicarboxylates in 70-90% yield via electrochemically induced oxidative rearrangement. Acidification of the reaction mixture after the electrolysis leads to the formation of 2-alkyl-3-oxoalkane-1,1- dicarboxylates. In the case of isobutylidenemalonate, the electrolysis intermediate dimethyl 3,3-dimethyl-2-methoxy-cyclopropane-1,1-dicarboxylate was isolated in 70% yield.
- Elinson, Michail N.,Feducovich, Sergey K.,Nikishin, Gennady I.
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p. 14529 - 14540
(2007/10/03)
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- Electrochemical Cyclodimerization of Alkylidenemalonates
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Electrolysis of dimethyl alkylidenemalonates RCH=C(COOMe)2 (R=n-Alk, Ph) in an undivided cell in MeOH in the presence of alkali metal halide as mediator, leads to the formation of cyclic dimers, i.e., 3,4-disubstituted 1,1,2,2-cyclobutanetetracarboxylates.The reaction proceeds via the reductive coupling of two substrate molecules at cathode and the cyclization of a hydrodimer dianion by its interaction with an active form of a mediator, an anode-generated halogen.
- Elinson, Michail N.,Feducovich, Sergey K.,Zakharenkov, Alexandre A.,Ugrak, Bogdan I.,Nikishin, Gennady I.,et al.
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p. 5035 - 5046
(2007/10/02)
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- Electrochemical cyclodimerization of alkylidenemalonates into 3,4-disubstituted cyclobutane-1,1,2,2-tetracarboxylates
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Alkylidenemalonates being electrolyzed in methanol in undivided cell with glassy carbon, carbon or lead cathode in the presence of sodium iodide or sodium bromide are transformed into 3,4-disubstituted cyclobutane-1,1,2,2-tetracarboxylates.
- Nikishin, Gennady I.,Elinson, Michail N.,Feducovich, Sergey K.,Ugrak, Bogdan I.,Struchkov, Yuri T.,Lindeman, Sergey V.
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p. 3223 - 3226
(2007/10/02)
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