Journal of the Chemical Society. Perkin transactions II p. 255 - 260 (1983)
Update date:2022-08-10
Topics:
Calvert, David J.
Mare, Peter B. D. de la
Suzuki, Hitomi
The chlorinations of 1-methyl-2-naphthol, 1-bromo-2-naphthol, 2,2'-dihydroxy-1,1'-dinaphthylmethane, and 6-t-butyl-2-naphthol with excess of chlorine in acetic acid give tetralin-2-ones analogous to that formed from 1-chloro-2-naphthol. 1,6-Di-t-butyl-2-naphthol, however, gives only 1,6-di-t-butyl-1,3-dichloro-1,2-dihydronaphthalene; 1-iodo-2-naphthol gives some 1,1,3,4-tetrachlorotetralin-2-one in acetic acid, whereas in chloroform it gives a mixture from which r-1,c-2,t-3,t-4,5,7-hexachlorotetralin-6-ol was isolated.The structures of these products and the pathways leading to them are discussed.
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