• 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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    • Keywords

       

      Steric enhancement of resonance; steric inhibition of resonance; Cr(VI) oxidation of 4-methoxyphenylmethycarbinols; reduction of substituted acetophenones with NaBH4

    • 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.

    • Author Affiliations

       

      V Baliah1 2 V Sundari1

      1. Department of Chemistry, Annamalai University, Annamalainagar - 608 002, India
      2. 79, 3rd Cross Road, Venkatanagar, Pondicherry - 605011, India
    • Dates

       
  • Journal of Chemical Sciences | News

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