Reaction of 1-(2-Oxocyclohexyl)ethane-1,1,2,2-tetracarbonitrile with α,β-Unsaturated Aldehydes

Abstract

The reaction of 1-(2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonitrile with crotonic aldehyde, cinnamic aldehyde, 2-furylacrolein, 3-phenyl-2-propinal, 3-butyl-2-propinal, and R-(−)-myrtenal have been investigated. It has been shown that these reactions proceed through the stage of the formation of 8a-hydroxyhexahydro-2H-chromene-3,3,4,4-tetracarbonitrile, followed by the formation of 10-iminotetrahydro-8a,4-(epoxymethane)chromene-3,3,4(2H,4aH-tricarboritrile. The X-ray diffraction data have suggested that the stereochemical features of the target products are determined by the reaction path.