Issue 10, 1995
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Nucleophilic coupling of alkali 2-naphthoxides with 1-bromo-2 naphthols. Ion-pairing and halogen dance in the formation of 1,1′-binaphthalene-2,2′-diols

Martin Bělohradský,   Petr Holý  and  Jiří Závada  

Abstract

A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the title product formation. A simple rationale has been provided assuming self assembly of the complementary reactants driven by hydrogen bonding and ion-pairing interactions. Concomitantly, halogen exchange between the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-naphthoxide attack at the bromine terminus of the Cα–Br bond in the participating 1-bromo-2-naphthol.

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Article information

DOI
https://doi.org/10.1039/P29950001853
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1995, 1853-1856

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Nucleophilic coupling of alkali 2-naphthoxides with 1-bromo-2 naphthols. Ion-pairing and halogen dance in the formation of 1,1′-binaphthalene-2,2′-diols

M. Bělohradský, P. Holý and J. Závada, J. Chem. Soc., Perkin Trans. 2, 1995, 1853 DOI: 10.1039/P29950001853

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