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Reinvestigation of the Reaction of Sodium Borohydrate with Benzhydryl Halides under Solvolytic Conditions
Authors:Kwang-Ting Liu  Huei-Chin Huang
Abstract: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.
Keywords:Benzhydryl bromide  Benzhydryl chlorides  Sodium borohydride  Solvolysis  Carbocation
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