Reaction of organoboranes with neutral hydrogen peroxide

Abstract

Tri-n-hexylborane reacts vigorously with neutral aqueous hydrogen peroxide with the cleavage of two of the three boron–carbon bonds, to give a mixture of hydrocarbons and n-hexanol. In particular, good yields of dimeric hydrocarbons are formed. When the reaction is performed in carbon tetrachloride solution, the yield of dimer decreases and is replaced by alkyl chlorides and more alcohol. The reaction is applied to other organoboranes.