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The Ireland–Claisen rearrangement is a chemical reaction of an allylic ester with strong base to give an γ,δ-unsaturated carboxylic acid. [1] [2] [3]
The Claisen rearrangement is a powerful carbon–carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen. [1] The heating of an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to give a γ,δ-unsaturated carbonyl, driven by exergonically favored carbonyl CO bond formation Δ(Δ f H) = −327 kcal/mol (−1,370 kJ/mol).
[11] [12] [13] This rearrangement is a useful carbon-carbon bond-forming reaction. An example of Claisen rearrangement is the [3,3] rearrangement of an allyl vinyl ether, which upon heating yields a γ,δ-unsaturated carbonyl. The formation of a carbonyl group makes this reaction, unlike other sigmatropic rearrangements, inherently irreversible.
The reaction is known as the Claisen reaction and was described by Claisen for the first time in 1890. Discovered the thermally induced rearrangement of allyl phenyl ether in 1912. He details its reaction mechanism in his last scientific publication (1925). In his honor, the reaction has been named the Claisen rearrangement.
Claisen may refer to: Rainer Ludwig Claisen, a German chemist Claisen rearrangement, a reaction of a allyl vinyl ether to a γ,δ-unsaturated carbonyl; Claisen condensation, a reaction between esters and carbonyl compounds in the presence of a strong base; Ireland–Claisen rearrangement, a chemical reaction of an allylic ester with strong base
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.
In [1,j]-sigmatropic rearrangements if j + 1 = 4n, then supra/antara is thermally allowed, and if j + 1 = 4n + 2, then supra/supra or antara/antara is thermally allowed. [20] The other prevalent class of sigmatropic rearrangements are [3,3], notably the Cope and Claisen rearrangements. Here, the constructive interactions must be between the ...
The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β-diketone. [1] It is named after Rainer Ludwig Claisen, who first published his work on the reaction in 1887.