Synthesis, chemistry and photochemistry of cyanobutadiyne (HCCCCCN)

Cyanobutadiyne has been synthesized starting from the mono or bistributylstannyl derivative of 1,3-butadiyne and p-toluenesulfonyl cyanide. The UV spectrum of HC5N and the 13C NMR spectrum of the deuterocyanobutadiyne DC5N have been recorded for the first time. Cyanobutadiyne has been detected in the photolysis of mixtures of gases observed on Titan. Its formation starting from cyanoacetylene and acetylene also occurs in the presence of huge amounts of dinitrogen, the major constituent of the Titan’s atmosphere. The application of these findings to the atmosphere of Titan is discussed. The chemistry and photochemistry of cyanobutadiyne have been investigated. A photoadduct has been observed in the photolysis of cyanoacetylene and ethanethiol and, a univocal synthesis of this compound was performed by a nucleophilic addition reaction.