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Proton-Transfer Reactions pp 339–384Cite as

Neighbouring Group Participation

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Abstract

Neighbouring-group participation in proton-transfer reactions is generally referred to as intramolecular general-acid or intramolecular general-base catalysis [1]. Two types are possible. The first involves an intramolecular proton transfer, either abstraction of a proton from a reacting functional group by an internal base or donation of a proton to one by an internal acid. The intramolecularly general-base catalysed enolization of the anion of 2-carboxy-acetophenone (see p. 370) and the intramolecularly general-acid catalysed hydrolysis of 2-methoxy-methoxybenzoic acid (see p. 342) are examples of reactions which are thought to involve processes of this type. In the second type the proton transfer is intermolecular with attack of a nucleophile on one functional group of a molecule being facilitated by proton abstraction by a second basic functional group. The intramolecularly general-base catalysed hydrolysis of the anion of phenyl salicylate (see p. 348) is a reaction which is thought to involve a process of this type.

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  1. Brian Capon
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Editors and Affiliations

  1. University Chemical Laboratory, University of Kent, Canterbury, New Zealand

    Edward Caldin

  2. Department of Chemistry, King’s College, London, UK

    Victor Gold F.R.S.

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Capon, B. (1975). Neighbouring Group Participation. In: Caldin, E., Gold, V. (eds) Proton-Transfer Reactions. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-3013-2_11

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