ORGANOBORANES. XXXIII. PROTONOLYSIS OF TRIETHYLBORANE WITH CARBOXYLIC ACIDS

Article abstract of DOI:10.1016/0022-328X(83)87016-8

The hydrolysis of triethylborane with water proceeds very slowly at room temperature, unaffected by hydrochloric acid, but inhibited by sodium hydroxide.Acetic acid, however, removes the first ethyl group rapidly, followed by a slower removal of the second.The protonolysis of the third ethyl group requires elevated temperatures.The unusual reactivity of carboxylic acid toward protonolysis of triethylborane is attributed to the presence of both acidic and basic sites in close proximity.The effect of added reagents is also studied.Thus, bases, such as pyridine, inhibit the removal of the first ethyl group, whereas, hydroxylic solvents, water, and strong acids and bases hinder protonolysis of the second ethyl group.