High-yield formation of substituted tetracyanobutadienes from reaction of ynamides with tetracyanoethylene

Abstract

A high-yielding sequence of [2+2] cycloaddition-retroelectrocyclization of ynamides with tetracyanoethylene (TCNE) is described. The reaction provided tetracyanobutadiene (TCBD) species, which were characterized by various techniques. DFT and TD-DFT calculations were also performed to complement experimental findings.

Keywords: [2+2] cycloaddition; tetracyanobutadienes; tetracyanoethylene; ynamides.