124287-32-7Relevant academic research and scientific papers
Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; S(N)2 substitution at boron atom
Charoy,Valleix,Toupet,Le Gall,Van Chuong,Mioskowski
, p. 2275 - 2276 (2007/10/03)
Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an S(N)2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.
Synthesis and characterization of amine-alkylcyanoboranes
Mills, Wyatt J.,Sutton, Christopher H.,Libby, Eduardo,Todd, Lee J.
, p. 302 - 308 (2008/10/08)
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-alkylcyanoboranes (amine = Me3N, py, TMED, quinuclidine; alkyl = methyl, benzyl, sec-butyl, isobutyl) in moderate yield. The new amine-alkylcyanoboranes are thermally, oxidatively, and hydrolytically stable and can be purified by using standard chromatographic methods.
