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Issue 9, 1970
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Reactions of tetrahalogeno-1,2-benzoquinones. Part III. Reaction of tetrachloro-1,2-benzoquinone with tetralones and naphthols: pathway to the condensates

Abstract

With a view to understanding the mechanism of the formation of 6-methoxy-2,2-(tetrachloro-o-phenylenedioxy)-naphthalen-1 (2H)-one (IIIa) in the reaction of 6-methoxy-1-tetralone (Ia) with tetrachloro-1,2-benzoquinone (II), the reaction of (II) with various tetralones and naphthols has been studied. Reaction with either α-tetralone or α-naphthol gives 2,2-(tetrachloro-o-phenylenedioxy)naphthalen-1 (2H)-one (IIIb), whereas reaction with either β-tetralone or β-naphthol gives a mixture of (IIIb) and 1,1-(tetrachloro-o-phenylenedioxy)-naphthalen-2(1H)-one (IX), with the former predominating. Further, reactions of (II) with 7-methoxy-3,4-dihydrophenanthren-1(2H)-one and m-methoxyphenol gave respectively 7-methoxy-2,2-(tetrachloro-o-phenylenedioxy)phenanthren-1 (2H)-one (VII) and 3-methoxy-6,6-(tetrachloro-o-phenylenedioxy)cyclohexa-2,4-dien-1-one (VIII). Structures of all these compounds have been proved on the basis of i.r. and n.m.r. data. The pathway to the formation of the condensates (III) is discussed.

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Article type: Paper
DOI: 10.1039/J39700001257
Citation: J. Chem. Soc. C, 1970,0, 1257-1259
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    Reactions of tetrahalogeno-1,2-benzoquinones. Part III. Reaction of tetrachloro-1,2-benzoquinone with tetralones and naphthols: pathway to the condensates

    T. R. Kasturi, T. Arunachalam and G. Subrahmanyam, J. Chem. Soc. C, 1970, 0, 1257
    DOI: 10.1039/J39700001257

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