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A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. [1] The reaction is named for Nobel Prize winning chemist Georg Wittig. [2] [3] The intermediate is an alkoxy lithium salt, and the final product an alcohol.
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. [1] [2] [3] Most often, the Wittig reaction is used to introduce a methylene group using ...
A pericyclic reaction is a type of reaction with multiple carbon–carbon bond making and breaking wherein the transition state of the molecule has a cyclic geometry, and the reaction progresses in a concerted fashion. Examples are hydride shifts. and the Claisen rearrangement: [5]
The [2,3]-Wittig rearrangement is the transformation of an allylic ether into a homoallylic alcohol via a concerted, pericyclic process. Because the reaction is concerted, it exhibits a high degree of stereocontrol, and can be employed early in a synthetic route to establish stereochemistry.
Winstein reaction; Wittig reaction; Wittig rearrangement: 1,2-Wittig rearrangement; 2,3-Wittig rearrangement; Wittig–Horner reaction; Wohl degradation; Wohl–Aue reaction; Wohler synthesis; Wohl–Ziegler reaction; Wolffenstein–Böters reaction; Wolff rearrangement; Wolff–Kishner reduction; Woodward cis-hydroxylation; Woodward–Hoffmann ...
The Corey–Fuchs reaction is based on a special case of the Wittig reaction, where two equivalents of triphenylphosphine are used with carbon tetrabromide to produce the triphenylphosphine-dibromomethylene ylide. [2] Step 1 of the Corey-Fuchs reaction, generating the active ylide. This ylide undergoes a Wittig reaction when exposed to an aldehyde.
For example they usually fail to react with ketones, necessitating the use of the Horner–Wadsworth–Emmons reaction as an alternative. Such stabilized ylides usually give rise to an E-alkene product when they react, rather than the more usual Z-alkene.
The Julia olefination (also known as the Julia–Lythgoe olefination) is the chemical reaction used in organic chemistry of phenyl sulfones (1) with aldehydes (or ketones) to give alkenes (olefins)(3) after alcohol functionalization and reductive elimination using sodium amalgam or SmI 2.