TY - JOUR
T1 - Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles
AU - Fallon, Gary D.
AU - Fitzmaurice, Neil J.
AU - Jackson, W. Roy
AU - Perlmutter, Patrick
PY - 1985/1/1
Y1 - 1985/1/1
N2 - By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.
AB - By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.
UR - http://www.scopus.com/inward/record.url?scp=33644577067&partnerID=8YFLogxK
U2 - 10.1039/c39850000004
DO - 10.1039/c39850000004
M3 - Article
AN - SCOPUS:33644577067
SP - 4
EP - 5
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
SN - 0022-4936
IS - 1
ER -