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Paper | Regular issue | Vol 53, No. 2, 2000, pp.359-372
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8786
New Reduction Reaction of Benzylic Alcohols with Acid and Proof of the Intermolecular Hydride Shift Mechanism

Masaru Kihara,* Jun-ichi Andoh, and Chiaki Yoshida

*Graduate of School of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan

Abstract

The new reduction reaction of the hydroxy groups of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinolines (1) to the corresponding alkanes (2) with mineral and Lewis acids is reported. A stereoselective intermolecular hydride shift mechanism of the reduction was proved by reaction of the deuterated derivateives (14 and 15) of 1a with 10N HCl-C2H5OH and BBr3 in CH3CN.