Abstract
Abstract The steric hindrance in the O-alkylation of PhOK by alkyl acetate (PhOK+AcOR→PhOR+AcOK) was examined by means of competitive reactions. As a result, the following sequence of the reactivities of alkyl acetates was obtained: CH3>>C2H5>n-C3H7\gtrsimn-C4H9>s-C4H9>i-C3H7\gtrsimi-C4H9>t-C4H9 and n-C4H9>n-C5H11>i-C5H11. The electronic effect in the O-alkylation was also examined by means of the competitive reaction of p-substituted (CH3 or CH3O) methyl benzoate and methyl benzoate with PhOK. The reactivity decreases in the following order: C6H5COOMe>p-CH3C6H4COOMe>p-CH3OC6H4COOMe. Therefore, it was concluded that the rate-determining step is the attack of the phenoxide anion on the carbon atom of the methyl group.
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