Sodium trialkylcyanoborates

Vinylic copper reagents react with CICN to give vinyl cyanides, though BrCN and ICN give the vinylic halide instead." Vinylic cyanides have also been prepared by the reaction between vinylic lithium compounds and phenyl cyanate PhOCN." Alkyl cyanides (RCN) have been prepared, in varying yields, by treatment of sodium trialkylcyanoborates with NaCN and lead tetraacetate." Vinyl bromides reacted with KCN, in the presence of a nickel complex and zinc metal to give the vinyl nitrile. Vinyl triflates react with LiCN, in the presence of a palladium catalyst, to give the vinyl nitrile." ... 

Cyanoboration (4, 445-447 5, 446-447) ketone synthesis. Symmetrical ketones can be prepared in high yield by conversion of trialkylboranes into sodium trialkylcyanoborates (1) by reaction with sodium cyanide. Reaction of (1) with an electrophile (an imidoyl chloride, benzoyl chloride, or especially,... 

---