Kasturi, T. R. ; Sivaramakrishnan, R. (1978) Reactions of tetrahalogeno-o-benzoquinones-Part VII. Reaction of alkyl-2-naphthols with tetrachloro-o-benzoquinone Proceedings of the Indian Academy of Sciences - Chemical Sciences, 87 (3). pp. 181-187. ISSN 0253-4134
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Official URL: http://www.ias.ac.in/j_archive/chemsci/87/2/181-18...
Related URL: http://dx.doi.org/10.1007/BF03182129
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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Indian Academy of Sciences. |
Keywords: | Oxidation; O-chloranil; Alkyl Naphthols; NMR Spectra and Dienones |
ID Code: | 16137 |
Deposited On: | 15 Nov 2010 14:08 |
Last Modified: | 17 May 2016 00:57 |
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