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

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.