Synthesis and characterization of amine-alkylcyanoboranes

Abstract

Synthetic methods for the conversion of alkyltrihydroborates to amine-alkylcyanoboranes have been developed. The most efficient of these is cyanation of the alkyltrihydroborates with mercuric cyanide to give the corresponding alkylcyanodihydroborates. These stable salts, when treated with 1 equiv of HCl in diethyl ether, followed by addition of an amine, produce the amine-alkyl-cyanoboranes (amine=Me 3 N, py, TMED, quinuclidine; alkyl=methyl, benzyl, sec-butyl, isobutyl) in moderate yield. The new amine-alkylcyanoboranes are thermally, oxidatively, and hydrolytically stable