Hydrocyanation of α,ω-Diynes Catalyzed by Tetracyanonickelate. Regiospecific Synthesis of a New Series of Acyclic Dinitriles

Article abstract of DOI:10.1246/bcsj.56.2863

Hydrocyanation of α,ω-diynes without the use of HCN has been described.Cyanonickelate, prepared by reducing ^2- with NaBH4 or Zn in the presence of excess KCN in water or ethylene glycol, catalyzes hydrocyanation of α,ω-diynes, HC<*>C(CH2)nC<*>CH to give quantitatively CH3CH(CN)(CH2)nCH(CN)CH3, a new series of acyclic dinitriles.Importance of the preliminary formation of a (?-acetylene)nickel(0) complex for the hydrocyanation has been suggested.