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

DOI: 10.1039/P29950001853

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1853 - 1856 (1995)

Update date:2022-09-26

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Authors:

Belohradsky, Martin

Holy, Petr

Zavada, Jiri

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Article abstract of DOI:10.1039/P29950001853

A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the 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-napthoxide attack at the bromide terminus of the C_α-Br bond in the participating 1-bromo-2-naphthol.

Full text of DOI:10.1039/P29950001853

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