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

Kasturi , TR and Sivaramakrishnan, R (1978) Reactions of tetrahalogeno-o-benzoquinones—Part VII. Reaction of alkyl-2-naphthols with tetrachloro-o-benzoquinone. In: Proceedings of the Indian Academy of Sciences - Section A, 87 (6). 181-187 .

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Abstract

Reaction of 8-methyl-2-naphthol (4a) with the quinone3 gave a mixture of 8-methyl-2,2-(tetrachlorohenylenedioxy)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--henylenedioxy)-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--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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Indian Academy of Sciences.
Keywords: Oxidation -o-chloranil - alkyl naphthols - NMR spectra and dienones For Part VI see Kasturi and Sivaramakrishnan (1977).
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 21 Oct 2010 05:42
Last Modified: 21 Oct 2010 05:42
URI: http://eprints.iisc.ernet.in/id/eprint/33331

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