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The Ireland–Claisen rearrangement is a type of Claisen rearrangement. The mechanism is therefore a concerted [3,3]-sigmatropic rearrangement which according to the Woodward–Hoffmann rules show a concerted, suprafacial, pericyclic reaction pathway.
The Ireland–Claisen rearrangement is the reaction of an allylic carboxylate with a strong base (such as lithium diisopropylamide) to give a γ,δ-unsaturated carboxylic acid. [25] [26] [27] The rearrangement proceeds via silylketene acetal, which is formed by trapping the lithium enolate with chlorotrimethylsilane. Like the Bellus-Claisen ...
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
Robert E. Ireland (1929 – February 4, 2012) was an American chemist and the Thomas Jefferson Chair Professor of chemistry at the University of Virginia. He is known for his textbook Organic Synthesis [ 1 ] and his contributions to the Ireland–Claisen rearrangement chemical reaction.
The Chugaev elimination is a chemical reaction that involves the elimination of water from alcohols to produce alkenes.The intermediate is a xanthate.It is named for its discoverer, the Russian chemist Lev Aleksandrovich Chugaev (1873–1922), who first reported the reaction sequence in 1899.
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.
A modified Ireland-Claisen rearrangement leads to tetrahydropyridines via a silyl ketene acetal intermediate. [ 3 ] Ring-closing olefin metathesis has also been used to establish the tetrahydropyridine ring system.
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.