• Oxidation of gem-chloronitroso- and vic-chloronitroso-alkanes and -cycloalkanes to respective chloronitro compounds by novel cetyltrimethylammonium hypochlorite reagent

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    • Keywords


      Cetyltrimethylammonium hypochlorite; oxidation; gem-chloronitroso compounds; vic-chloronitroso compounds; gem-chloronitro compounds; vic-chloronitro compounds; nitroso-to-nitro conversion; nitrosyl chloride; oxime.

    • Abstract


      Cetyltrimethylammonium hypochlorite (CTAHC) is prepared and used as an oxidizing agent for nitroso group to nitro group. The gem-chloronitroso and vic-chloronitroso compounds are prepared respectively from ketoximes and olefins by reacting with NOCl generated in situ from chlorotrimethylsilane (TMSCl) and iso-amyl nitrite. CTAHC oxidizes gem-chloronitroso and vic-chloronitroso compounds to the corresponding chloronitro derivatives. While gem-chloronitro compounds are obtained in good yields, the vic-chloronitro derivatives are formed in moderate yields, because of the propensity of the vic-chloronitroso group to tautomerize to 𝛼-chlorooxime. The present method is simple and practical, particularly for the preparation of vic-chloronitro compounds, considering the fact that the known methods of their preparation are few and quite involved.

    • Author Affiliations


      Abdulkarim H A Mohammed1 2 Gopalpur Nagendrappa1

      1. Department of Chemistry, Bangalore University, (Central College Campus), Bangalore 560 001, India
      2. University of Sana’a, Sana’a, Yemen
    • Dates

  • Journal of Chemical Sciences | News

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      Posted on July 25, 2019

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