The rates of oxidation of 3-substituted-4-methoxyphenylmethylcarbinols with Cr(VI) have been measured. The results show that the mesomeric effect of the methoxy group in 3-substituted-4-methoxyphenylmethylcarbinols is greater than that in 4-methoxyphenylmethylcarbinol even after taking the polar effect of the 3-substituent into consideration, indicating that the adjacent 3-substituent sterically enhances the resonance of the 4-methoxy group. The expected steric inhibition of resonance is observed in 3,5-disubstituted-4-methoxyphenylmethylcarbinols. The rates of reduction of some substituted acetophenones with sodium borohybride furnish additional evidence for steric enhancement of resonance.
Volume 134, 2022
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