Organosilver(I) chemistry: On the reaction of RAg and R2AgMgCl compounds with conjugated enynenitriles

The addition of RAg and R₂AgMgCl to enynenitriles

is described. RAg reagents prefer to transfer their R group to the double bond of these nitriles, so that after protolysis 2,3-alkadienenitriles are obtained, while the homoargentates generally give 2,4-alkadienenitriles. The regio- and stereo-chemical course of the reactions are compared with those in additions of RCu and R₂CuMgCl to the enynenitriles.