960305-76-4Relevant articles and documents
An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst
Hussein,Huynh,Hommelsheim,Koenigs,Nguyen
supporting information, p. 12970 - 12973 (2018/11/23)
The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C-C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Br?nsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.
Retro-claisen condensation with FeIII as catalyst under solvent-free conditions
Rao, Chitturi Bhujanga,Rao, Dasireddi Chandra,Babu, Dokuburra Chanti,Venkateswarlu, Yenamandra
supporting information; experimental part, p. 2855 - 2859 (2010/08/05)
An iron(III) salt catalyzed retro-Claisen condensation between an alcohol and a 1,3-diketone was investigated. The mechanism involves the formation of a metal-induced sixmembered cyclic transition state and cleavage of the C sp2-Csp3 bond. Regioselective esterification and one-pot couversion of silyl ethers into esters with good yields was observed. Simple reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method.