• Reactions of tetrahalogeno-o-benzoquinones—Part VII. Reaction of alkyl-2-naphthols with tetrachloro-o-benzoquinone

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      https://www.ias.ac.in/article/fulltext/jcsc/087/06/0181-0187

    • Keywords

       

      Oxidation; o-chloranil; alkyl naphthols; NMR spectra and dienones

    • Abstract

       

      Reaction of 8-methyl-2-naphthol (4a) with the quinone3 gave a mixture of 8-methyl-2,2-(tetrachloro-o-phenylenedioxy)naphthalen-1(2H)-one (1b) and 8-methyl-1,1-(tetrachloro-o-phenylenedioxy)naphthalen-2(1H)-one (2b) in almost equal amounts. Similarly, reaction of the naphthols (4b), (4d) and (4e) with3 gave the corresponding dienones (1c &2c), (1e &2e) and (1f &2f) in almost equal amounts. Reaction of 8-t-butyl-2-naphthol (4c) with3 gave exclusively 8-t-butyl-2,2-(tetrachloro-o-phenylenedioxy)-naphthalen-1(2H)-one (1d). Oxidation of 3-t-butyl-2-naphthol (4f) with3 gave a mixture of 3-t-butyl-2,2-(tetrachloro-o-phenylendioxy) nephthalene-1(2H)-one(1g) and 3-t-butyl-1,1-(tetrachloro-o-phenylenedioxy)naphthelen-2 (1H)-one (2g) in the ratio 1∶6. Thus, onlyt-butyl group exherts pronounced steric influence on the rearrangement observed in the reaction of β-naphthol with the quinone3. Structures of all the compounds have been established by spectral data.

    • Author Affiliations

       

      T R Kasturi1 R Sivaramakrishnan1

      1. Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012
    • Dates

       
  • Journal of Chemical Sciences | News

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