Hydrocyanation of α,ω-Diynes Catalyzed by Tetracyanonickelate. Regiospecific Synthesis of a New Series of Acyclic Dinitriles
- 1 September 1983
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 56 (9) , 2863-2864
- https://doi.org/10.1246/bcsj.56.2863
Abstract
Hydrocyanation of α,ω-diynes without the use of HCN has been described. Cyanonickelate, prepared by reducing [Ni(CN)4]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 (π-acetylene)nickel(0) complex for the hydrocyanation has been suggested.This publication has 2 references indexed in Scilit:
- Nickel(0) catalysed additions of hydrogen cyanide to alkynes: stereochemistry, mechanism, and preparative applicationJournal of the Chemical Society, Chemical Communications, 1982
- Hydrogenolysis of unsaturated alcohols; hydrocyanation and hydrogenation of acetylenes catalysed by pentacyanocobaltate(II)Journal of the Chemical Society, Chemical Communications, 1978