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 .
PDF
part.pdf - Published Version Download (549kB) |
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 |
---|---|
Publication: | Proceedings of the Indian Academy of Sciences - Section A |
Publisher: | Indian Academy of Sciences |
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.ac.in/id/eprint/33331 |
Actions (login required)
View Item |