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Issue 12, 1976
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The kinetics and mechanisms of aromatic halogen substitution. Part XXXIII. Kinetics and products of chlorination of some aryl acetates

Abstract

The rates and products of reaction of 4-methylphenyl acetate, 3,4- and 2,6-dimethylphenyl acetate, and 2,3,5,6-tetramethylphenyl acetate with molecular chlorine in acetic acid have been studied. ‘Abnormal’ reaction paths play a large part in the determination of the products of the chlorination of the first two of these compounds, probably through electrophilic attack on an activated ‘ipso’-position. The observed rates of reaction are compared with those calculated on the basis of additivity of substituent effects; they allow an estimate to be made of the effect of steric inhibition of resonance on the directing power of the acetoxy-group. The product of chlorination of the corresponding phenols are recorded also.

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Article type: Paper
DOI: 10.1039/P29760001389
J. Chem. Soc., Perkin Trans. 2, 1976, 1389-1396

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    The kinetics and mechanisms of aromatic halogen substitution. Part XXXIII. Kinetics and products of chlorination of some aryl acetates

    P. B. D. de la Mare, B. N. B. Hannan and N. S. Isaacs, J. Chem. Soc., Perkin Trans. 2, 1976, 1389
    DOI: 10.1039/P29760001389

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