Chemical acetal cleavage mechanism

Earlier suggestions of stereoelectronic control of acetal cleavage for the lysozyme reaction Gorenstein, D. G., Findlay, J. B., Luxon, B. A., Kar, D. (1977). Stereoelectronic control in carbon-oxygen and phosphorus-oxygen bond breaking processes. Ah initio calculations and speculations on the mechanism of action of ribonuclease A, staphylococcal nuclease, and lysozyme. Journal of the American Chemical Society, 99, 3477. 

Physical and Chemical Properties. The (F)- and (Z)-isomers of cinnamaldehyde are both known. (F)-Cinnamaldehyde [14371-10-9] is generally produced commercially and its properties are given in Table 2. Cinnamaldehyde undergoes reactions that are typical of an a,P-unsaturated aromatic aldehyde. Slow oxidation to cinnamic acid is observed upon exposure to air. This process can be accelerated in the presence of transition-metal catalysts such as cobalt acetate (28). Under more vigorous conditions with either nitric or chromic acid, cleavage at the double bond occurs to afford benzoic acid. Epoxidation of cinnamaldehyde via a conjugate addition mechanism is observed upon treatment with a salt of /-butyl hydroperoxide (29). 

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