Electrochemical cyclodimerization of alkylidenemalonates

Authors

Michail N. Elinson, Russian Academy of SciencesFollow
Sergey K. Feducovich, Russian Academy of SciencesFollow
Alexandre A. Zakharenkov, Russian Academy of Sciences
Bogdan I. Ugrak, Russian Academy of Sciences
Gennady I. Nikishin, Russian Academy of SciencesFollow
Sergey Lindeman, Marquette UniversityFollow
Jurii T. Struchkov, Russian Academy of SciencesFollow

Document Type

Article

Language

eng

Publication Date

4-1995

Publisher

Elsevier

Source Publication

Tetrahedron

Source ISSN

0040-4020

Abstract

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.

Comments

Tetrahedron, Vol. 51, No. 17 (April 24, 1995): 5035-5046. DOI.

Sergey V. Lindeman was affiliated with A.N. Nesmeyanov Institute of Organoelement Compounds, The Russian Academy of Sciences, Moscow, Russia at the time of publication.

Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/645