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The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. [1] The Horner–Wadsworth–Emmons reaction. In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions.
Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base.
Réaction de Horner-Wadsworth-Emmons; Usage on it.wikipedia.org Reazione di Horner-Wadsworth-Emmons; Usage on it.wikibooks.org Chimica organica/Cose da fare; Usage on ja.wikipedia.org ホーナー・ワズワース・エモンズ反応; Usage on nl.wikipedia.org Horner-Wadsworth-Emmons-reactie; Usage on pt.wikipedia.org Reação de Horner ...
Doebner modification; Doebner reaction; Doebner–Miller reaction, Beyer method for quinolines; Doering–LaFlamme carbon chain extension; Dötz reaction; Dowd–Beckwith ring expansion reaction; Duff reaction; Dutt–Wormall reaction; Dyotropic reaction
Ordinarily, the Horner–Wadsworth–Emmons reaction provides the (E)-enoate (α,β-unsaturated ester), just as the Wittig reaction does. To obtain the (Z)-enolate, the Still-Gennari modification of the Horner-Wadsworth-Emmons reaction can be used.
William D. Emmons (November 18, 1924 – December 8, 2001) was an American chemist and published with William S. Wadsworth a modification to the Wittig-Horner reaction using phosphonate-stabilized carbanions, now called the Horner-Wadsworth-Emmons reaction in his honor.
Organic reactions can be organized into several basic types. Some reactions fit into more than one category. For example, some substitution reactions follow an addition-elimination pathway. This overview isn't intended to include every single organic reaction. Rather, it is intended to cover the basic reactions.
The Horner-Wadsworth-Emmons reaction is a widely used olefination reaction in which a phosphonate-stabilized carbanion reacts with an aldehyde or ketone to form an alkene. In the standard HWE reaction, the phosphonate ester contains alkoxy substituents (typically methoxy or ethoxy), producing an E -alkene as the major product.