Abstract
The oxidation of a few methyl naphthols with tetrachloro-o-benzoquinone (1) has been described. Reaction of 1-methyl-2-naphthol (4) with the quinone (1) was found to give the spirodimer, 1,1′,2,2′-tetrahydro-3H-benzo (f) chromen-3-spiro-1′-naphthalene-2′-one (6) and a yellow solid which has been assigned the structure of 5,6,7,8-tetrachloro-1,4-benzodioxan-2-spiro-1′-naphthalen-2′-one (7) on the basis of chemical and spectral data. Among the other naphthols studied, 4-methyl-2-t-butyl-1-naphthol afforded 5,6,7,8-tetrachloro-1,4-benzodioxan-2-spiro-1′-naphthalen-3′-t-butyl-4′-one (22) while 2-methyl-1-naphthol and 4-methyl-1-naphthol gave 2-methyl-4,4-(tetrachloro-o-phenylenedioxy) naphthalen-1(4H)-one(15) and 4-methyl-2,2-(tetrachloro-o-phenylenedioxy) naphthelen-1(2H)-one (19) respectively. The present study has shown that oxidation of suitably substituted naphthols with the quinone (1) gives rise to naphthoquinone methides.
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For Part V see:Indian J. Chem.,B14, 319 1976
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Kasturi, T.R., Sivaramakrishnan, R. Reactions of tetrahalogeno-o-benzoquinones part VI: Reactions of tetrachloro-o-benzoquinone with methyl naphthols—Formation of naphthoquinone methides. Proc. Indian Acad. Sci. 86, 309–316 (1977). https://doi.org/10.1007/BF03046845
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DOI: https://doi.org/10.1007/BF03046845