Cyanocarbons: A classic example of discovery‐driven research

Cyanocarbons are organic compounds bearing enough cyano functional groups to significantly alter their chemical properties. For example, tetracyanoethylene forms a stable anion radical, is a strong π acid, and readily substitutes its cyano groups. Tetracyanoethylene oxide reacts by addition across its carbon–carbon bond. Diazodicyanoimidazole cleaves nitrogen to form a superelectrophilic carbene, and pentacyanocyclopentadiene is about as acidic as perchloric acid. In this highlight, discovery‐driven research that fanned out from tetracyanoethylene to a multiperson effort at DuPont on cyanocarbon chemistry is narrated.