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Reactions Of Tetrahalogeno-o-benzoquinones—Part VII. Reaction Of Alkyl-2-naphthols With Tetrachloro-o-benzoquinone
| Content Provider | Indian Institute of Science (IISc) |
|---|---|
| Author | Kasturi, T. R. Sivaramakrishnan, R. |
| Copyright Year | 1978 |
| 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 (Sb(B-naphthol with the quinone3. Structures of all the compounds have been established by spectral data. |
| File Format | |
| Journal | PeerReviewed |
| Language | English |
| Publisher | Indian Academy of Sciences |
| Publisher Date | 1978-01-01 |
| Access Restriction | Authorized |
| Subject Keyword | Organic Chemistry |
| Content Type | Text |
| Resource Type | Article |
