Expanding the chemical space for push-pull chromophores by non-concerted [2 + 2] and [4 + 2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

摘要

Non-concerted [2 + 2] and |4 + 2] cycloadditions between N,N-dimethylanilino-substituted l,l,2,4,4-pentacyanobuta-l,3-diene and 4-ethynyl-.N,N-dimethylaniline are controlled by solvent polarity and provide access to a highly functionalised 6,6-dicyanopentafulvene featuring an intense, low-energy charge-transfer band and to an unusual spirocyclic zwitterion, characterised by X-ray analysis.