Electrochemical cyclodimerization of alkylidenemalonates
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.; Lindeman, Sergey; and Struchkov, Jurii T., "Electrochemical cyclodimerization of alkylidenemalonates" (1995). Chemistry Faculty Research and Publications. 645.