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A novel mechanism for the NIH-shift.

H Yagi, D M Jerina, G J Kasperek

    Proceedings of the National Academy of Sciences of the United States of America
    |July 1, 1972
    PubMed
    Summary
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    The aromatization of 1,4-dimethylbenzene oxide yields 2,5-dimethylphenol and 2,4-dimethylphenol via an NIH-Shift. This reaction mechanism, studied across a wide pH range, offers insights into arene oxide chemistry and carcinogenesis.

    Area of Science:

    • Organic Chemistry
    • Chemical Kinetics
    • Biochemistry

    Background:

    • Arene oxides are reactive intermediates implicated in chemical carcinogenesis.
    • Understanding their transformation pathways is crucial for assessing toxicological risks.
    • The NIH-Shift is a known rearrangement mechanism in aromatic compounds.

    Purpose of the Study:

    • To investigate the kinetics and mechanism of 1,4-dimethylbenzene oxide aromatization.
    • To elucidate the role of pH in the NIH-Shift during arene oxide rearrangement.
    • To establish a model for nucleophilic addition to arene oxides.

    Main Methods:

    • Kinetic measurements of 1,4-dimethylbenzene oxide conversion to dimethylphenols across a pH range of 1-12.
    • Quantitative analysis of product ratios (2,5-dimethylphenol vs. 2,4-dimethylphenol) under spontaneous and acid-catalyzed conditions.

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  • Spectroscopic identification of reaction intermediates, where applicable.

    • Main Results:

    • The reaction rate follows the equation -d[I]/dt = [I][k(0) + (k[unk] + k[unk])aH].
    • Product ratios significantly differ between spontaneous (13:87) and acid-catalyzed (54:46) rearrangements.
    • A novel NIH-Shift mechanism involving nucleophilic addition via a diol intermediate was identified.

    Conclusions:

    • The NIH-Shift in 1,4-dimethylbenzene oxide is pH-dependent, influencing product distribution.
    • A new mechanism involving nucleophilic addition to arene oxides was demonstrated.
    • This study provides a model relevant to the metabolic activation of polycyclic aromatic hydrocarbons in carcinogenesis.