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Reinvestigation of the Reaction of Sodium Borohydrate with Benzhydryl Halides under Solvolytic Conditions
Author(s) -
Liu KwangTing,
Huang HueiChin
Publication year - 1997
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199700038
Subject(s) - chemistry , solvolysis , sodium borohydride , halide , carbocation , diglyme , substituent , aqueous solution , sodium , medicinal chemistry , inorganic chemistry , organic chemistry , hydrolysis , catalysis , solvent
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.