Reinvestigation of the Reaction of Sodium Borohydrate with Benzhydryl Halides under Solvolytic Conditions

Article abstract of DOI:10.1002/jccs.199700038

Solvolysis of benzhydryl halides in aqueous diglyme containing sodium borohydride was studied. Contrary to the literature, sodium borohydride was found not to be a convenient trap for benzhydryl carbocations, especially for those containing electron-withdrawing substituent, and it decomposed appreciably in 80% aqueous diglyme at 45 °C. In addition, significant acceleration of reactions due to the presence of sodium borohydride was realized in the solvolysis of 3-chloro- and 3-trifluoromethyl-benzhydryl chlorides.