First Kinetic Discrimination Between Carbon and Oxygen Reactivity of Enols

García‐Río, Luis; Mejuto, J. C.; Parajó, M.; Pérez‐Lorenzo, Moisés

doi:10.1021/jo801183y

Cited by 11 publications

References 65 publications

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Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Zeiger

Liebman

Ponikvar‐Svet

2017

Patai's Chemistry of Functional Groups

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In this chapter, we will discuss diverse aspects of the energetics of metal β‐diketonates and their derivatives. By “energetics” we mean thermochemical and related studies, and so we include enthalpies of reaction and of formation as well as equilibrium measurements and stability constants. We will also discuss the gain or loss of an electron, and therefore consider ionization potentials, electron affinities, and electrochemical potentials. By metal β‐diketonates and derivatives we mean, most generally, species with a substructure of the type [M(dik) n ], where dik (β‐diketonato) is an organic monovalent anion of structure (RC(X)C(R 1 )C(O)R 2 ) − and M is an arbitrary metal. For completeness and additional insights, in this chapter we will also consider M to be virtually all elements (nonmetal, metalloid, or metal), and eventually we will include hydrogen.

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Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Zeiger

Liebman

Ponikvar‐Svet

2017

Patai's Chemistry of Functional Groups

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Reactions of Aldehydes and Ketones and their Derivatives

Knipe¹

2011

Organic Reaction Mechanisms · 2008

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Enol Nitrosation Revisited: Determining Reactivity of Ambident Nucleophiles

et al. 2009

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Enols are one of the most important types of ambident nucleophiles being widely used as reagents in organic chemistry. The relevance of enols has led to considerable interest in developing methods to determine the reactivity of their nucleophilic centers. In this sense, the mainstream literature works on this topic make use of a combination of overall rate constants together with the analysis of the reaction products. By knowing the product ratio it is possible to determine the ratio between the reaction rates on each site. Thus, the reactivity for each nucleophilic position can be obtained. This is a reliable approach as long as the isolation or in situ characterization of the reaction products can be carried out. In the case of unstable and/or interconvertible products where the use of identification techniques is not possible, an alternative methodology must be found. For that reason, our research group has developed a model that allows us to study and quantify separately the reaction rates of enol nucleophilic centers even if only one final reaction product is obtained. This model is based on the fact that nitrosation of enols shows well‐differentiated behavior depending on whether the reaction proceeds through the carbon or the oxygen atom. The present study provides insights into the ambident nature of enols as well as a methodology for determining the chemical reactivity of their nucleophilic centers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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First Kinetic Discrimination Between Carbon and Oxygen Reactivity of Enols

Cited by 11 publications

References 65 publications

Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Reactions of Aldehydes and Ketones and their Derivatives

Enol Nitrosation Revisited: Determining Reactivity of Ambident Nucleophiles

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