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Maleic anhydride is a classic substrate for Diels-Alder reactions. [9] It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride is converted to many pesticides and pharmaceuticals.
Asymmetric Diels-Alder reaction is one step in the biosynthesis of the statin lovastatin. [60] The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6.
Styrene maleic anhydride copolymer is formed, retaining the aromaticity of the styrene. The Diels–Alder product can be re-aromatized using elemental sulfur at high temperature, followed by a second rearomatization by decarboxylation with barium hydroxide and copper: [3] Wagner-Jauregg reaction
In terms of the stereoselectivity of the reaction between maleic anhydride and cyclopentadiene, the endo-product is favored, a result best explained through FMO theory. The maleic anhydride is an electron-withdrawing species that makes the dieneophile electron deficient, forcing the regular Diels–Alder reaction.
The inverse electron demand Diels–Alder reaction, or DA INV or IEDDA [1] is an organic chemical reaction, in which two new chemical bonds and a six-membered ring are formed. It is related to the Diels–Alder reaction , but unlike the Diels–Alder (or DA) reaction, the DA INV is a cycloaddition between an electron-rich dienophile and an ...
Among the types of reactions that can be catalyzed by Lewis acids, those with carbonyl-containing substrates have received the greatest amount of attention.The first major discovery in this area was in 1960, when Yates and Eaton reported the significant acceleration of the Diels-Alder reaction by AlCl 3 when maleic anhydride is the dienophile.
Maleic anhydride is the precursor to various resins by copolymerization with styrene. Maleic anhydride is a dienophile in the Diels-Alder reaction. [7] Dianhydrides, molecules containing two acid anhydride functions, are used to synthesize polyimides and sometimes polyesters [14] and polyamides. [15]
Maleimide and its derivatives are prepared from maleic anhydride by treatment with amines followed by dehydration. [2] A special feature of the reactivity of maleimides is their susceptibility to additions across the double bond either by Michael additions or via Diels-Alder reactions.
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