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Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
Fukawa, Hidemichi,Suzuki, Kunio,Sekiya, Minoru
, p. 2868 - 2873 (2007/10/02)
The formic acid reduction of 1,1'-benzylidenedipiperidine (1) was kinetically investigated by the carbon dioxide trapping method.Rate data gave the rate equation, v=kobs.The initial mono- and diprotonation of 1 occur in equilibrium, and monoprotonated form is proposed to be an intermediate for the reduction to 1-benzylpiperidine.The isotope effect value (2.69) and the negative ρ substituent effect (similar to that of the formic acid reduction of N-benzylideneaniline) suggest that the reduction of 1 involves the same intermediate step of decarboxylation of the formic acid ester of the α-amino alcohol.
