Tetrahedron p. 5035 - 5046 (1995)
Update date:2022-07-30
Topics: Electrochemical Cyclodimerization Alkylidenemalonates
Elinson, Michail N.
Feducovich, Sergey K.
Zakharenkov, Alexandre A.
Ugrak, Bogdan I.
Nikishin, Gennady I.
et al.
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.
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