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Evidence suggests that the Wittig reaction of unbranched aldehydes under lithium-salt-free conditions do not equilibrate and are therefore under kinetic reaction control. [9] [10] E. Vedejs has put forth a theory to explain the stereoselectivity of stabilized and unstabilized Wittig reactions. [11]
The [1,2]-Wittig rearrangement, which produces isomeric pent-5-en-1-ols, is a competitive process that takes place at high temperatures. [2] Because of the high atom economy and stereoselectivity of the [2,3]-rearrangement, it has gained considerable synthetic utility.
An example of modest stereoselectivity is the dehydrohalogenation of 2-iodobutane which yields 60% trans-2-butene and 20% cis-2-butene. [5] Since alkene geometric isomers are also classified as diastereomers, this reaction would also be called diastereoselective.
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.
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular.
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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.
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