A new strategy of the chemical route to the cyclopropane structure: direct transformation of benzylidenemalononitriles and malononitrile into 1,1,2,2-tetracyanocyclopropanes

The new reaction was found: the direct formation of cyclopropanes from activated olefins and C-H acids. The action of free halogen or active halogen containing compounds on the equal amounts of benzylidenemalononitriles and malononitrile in basic alcohol solutions results in the formation of 3-aryl-1,1,2,2-tetracyanocyclopropanes in 65-95% yields. Thus, the new simple and efficient way to 3-aryl substituted tetracyanocyclopropanes was found directly from such simple and reasonable starting compounds as benzylidenemalononitriles and malononitrile.