Electrochemical Transformation of Malononitrile and Carbonyl Compounds into Functionally Substituted Cyclopropanes: Electrocatalytic Variant of the Wideqvist Reaction

Abstract Electrolysis of malononitrile and carbonyl compounds in the presence of alkali metal halides in an undivided cell results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 60–90% yield. This electrocatalytic variant of the Wideqvist reaction using malononitrile instead of bromomalonitrile was successfully performed. Electrocatalytic transformation of substituted 1,1,2,2-tetracyanocyclopropanes in methanol or ethanol in an undivided cell leads to substituted 2-amino-4,4-dialkoxy-1,5-dicyano-3-azabicyclo[3.1.0]hex-2-enes in 70–95% yields after 0.05–0.10 F/mol of electricity has been passed.