Volume 20, Issue 18
Isocyclic Compounds
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ChemInform Abstract: Direct Lithiation of Hydroxyaromatics.

G. COLL

G. COLL

Dep. Chem., Univ. Illes Balears, 07071 Palma de Mallorca, Spain

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J. MOREY

J. MOREY

Dep. Chem., Univ. Illes Balears, 07071 Palma de Mallorca, Spain

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A. COSTA

A. COSTA

Dep. Chem., Univ. Illes Balears, 07071 Palma de Mallorca, Spain

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J. M. SAA

J. M. SAA

Dep. Chem., Univ. Illes Balears, 07071 Palma de Mallorca, Spain

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First published: May 2, 1989

Abstract

Lithiation of 2-naphthol (I) with tert-butyllithium and subsequent treatment with the electrophilic compounds (II) results in regioselective formation of the 3-substituted 2-naphthols (III).

ChemInform Abstract

Lithiation of 2-naphthol (I) with tert-butyllithium and subsequent treatment with the electrophilic compounds (II) results in regioselective formation of the 3-substituted 2-naphthols (III). In contrast, 1-naphthol (V) gives a mixture of the mono- and disubstituted 1-naphthols (VI) - (VIII). Anthrone (XI) reacts with dimethyl disulfide (IIb), yielding 1-methylthioanthrone (XII) and 1-methylthio-9,10-anthraquinone (XIII).

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