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Kinetic evidence for steric enhancement of resonance: Oxidation of phenylmethylcarbinols with Cr(VI) and reduction of substituted acetophenones with sodium borohydride

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Abstract

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.

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  1. V Baliah

    Present address: , 79, 3rd Cross Road, Venkatanagar, 605011, Pondicherry, India

Authors and Affiliations

  1. Department of Chemistry, Annamalai University, 608 002, Annamalainagar, India

    V Baliah & V Sundari

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  1. V Baliah
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  2. V Sundari
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Baliah, V., Sundari, V. Kinetic evidence for steric enhancement of resonance: Oxidation of phenylmethylcarbinols with Cr(VI) and reduction of substituted acetophenones with sodium borohydride. Proc. Indian Acad. Sci. (Chem. Sci.) 101, 33–36 (1989). https://doi.org/10.1007/BF02869383

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  • DOI: https://doi.org/10.1007/BF02869383

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