A Mechanistic Study about the Formation of Tetracyanobutadienes Revealed an Autocatalytic Behavior

Abstract

AbstractIn a recent paper in Chemistry – A European Journal, Nielsen and coworkers reported a deep study on the mechanism of the [2+2] cycloaddition‐retroelectrocyclization (CA‐RE) between an electron‐rich alkyne and tetracyanoethylene (TCNE), inducing the formation of a 1,1,4,4‐tetracyanobutadiene (TCBD). Following a robust kinetic study, the authors confirmed important intermediates and determined this reaction to be autocatalytic for the first time. Given the increasing use of TCBDs in the community and the strength of the CA‐RE reaction this paper offers important insights for future developments of this promising reaction.