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The Carroll rearrangement is a rearrangement reaction in organic chemistry and involves the transformation of a β-keto allyl ester into a α-allyl-β-ketocarboxylic acid. This organic reaction is accompanied by decarboxylation and the final product is a γ,δ-allylketone. The Carrol rearrangement is an adaptation of the Claisen rearrangement and effectively a decarboxylative Allylation.
Additional recommended knowledge
The Carrol rearrangement (1940) in the presence of base and with high reaction temperature (path A) takes place through an intermediate enol which then rearranges in an electrocyclic Claisen rearrangement. The follow up is a decarboxylation. With palladium(0) as a catalyst, the reaction (Tsuji, 1980) is much milder (path B) with an intermediate allyl cation / carboxylic acid anion organometallic complex .
Asymmetric decarboxylative allylation
By introducing suitable chiral ligands, the reaction becomes enantioselective .
A similar reaction  uses additional naphthol.
The same catalyst but a different ligand is employed in this enantioconvergent reaction :
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Carroll_rearrangement". A list of authors is available in Wikipedia.|