Cinnamyl alcohol kinetics

Roth R, Boudet AM, Pont-Lezica R. Lignification and cinnamyl alcohol dehydrogenase activity in developing stems of tomato and popular a spatial and kinetic study through tissue printing. J Exp Bot 1997 48 247-254. 

C kinetic isotope effects (KIEs) of four cinnamyl alcohol oxidations have been determined by 13C NMR spectroscopy using competition reactions with reactants at natural 13C abundance. Primary 13C KIEs of the Pd(II)-catalysed oxidation and of the MnC>2 oxidation are similar ( 1.02) and indicate the C—H bond cleavages to be the irreversible and rate-limiting steps in the respective reactions. Low primary 13C KIEs in Swern and Dess-Martin oxidations, however, indicate that the initial C—H bond breakings and proton transfers are not the irreversible steps in these mechanisms, which control the rate.284... 

Dimitrova, R., Neinska,Y., Mihalyi, M. R., Tsoncheva, T. and Spassova, M., Catalytic activity of boron-beta zeolite modified with indium in the epoxidation of cinnamyl alcohol, Reaction Kinetics and Catalysis Letters 74(2), 353-362 (2001). 

The only kinetic study of acid-catalyzed isomerization of a simple allylic ether was published by Braude and Gore who found that methyl a-phenylallyl ether isomerizes to methyl cinnamyl ether in anhydrous dioxane containing either boron trifluoride or hydrogen chloride. At 25°C, the ether is a quarter to an eighth as reactive as the corresponding alcohol. 

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