Reference EntryDOI
The Dieckmann Condensation (Including the Thorpe‐Ziegler Condensation)
Reads0
Chats0
TLDR
The Dieckman condensation as mentioned in this paper is an acetoacetic ester condensation in which a dicarboxylic ester is cyclized to a beta-ketonic ester through the action of a base.Abstract:
The Dieckman condensation is an acetoacetic ester condensation in which a dicarboxylic ester is cyclized to a beta-ketonic ester through the action of a base. The dicarboxylic ester must have at least one alpha-hydrogen atom and the carbalkoxy groups must be situated that cyclization will result in a 4-membered ring or larger ring. Discovery and development of the reaction are generally credited to Dieckmann, who found that heating an adipic or a pimelic ester with sodium and a trace alcohol led to cyclization with formation of a cyclopentanone or a cyclohexanone. The Dieckmann condensation has proved useful for the preparation of a variety of carbocyclic and heterocyclic ketones and has been extended to the synthesis of 7 and 8-membered rings.
Keywords:
Dieckman condensation;
cyclizations;
Michael condensation;
intermolecular ester;
alkylation;
acyloin condensation;
failuresread more
Citations
More filters
Journal ArticleDOI
Stereoselective synthesis of sulfur-containing β-enaminonitrile derivatives through electrochemical Csp 3 –H bond oxidative functionalization of acetonitrile
TL;DR: An electro-oxidative C(sp3)–H bond functionalization of acetonitrile with thiols to afford tetrasubstituted olefins with high stereoselectivity is shown and can be easily scaled up.
Journal ArticleDOI
Determination of the pKa of cyclobutanone: Brønsted correlation of the general base-catalyzed enolization in aqueous solution and the effect of ring strain.
TL;DR: Comparison of the results for cyclobutanone to those previously reported for acetone and a 1-phenylacetone derivative indicated that the ring strain of the carbocycle appeared to have only a small effect on the general base-catalyzed rate constants for enolization.
Posted ContentDOI
Automatic discovery of chemical reactions using imposed activation
TL;DR: A simple computational approach that automatically and robustly explores chemical reaction pathways from knowledge only of the reactants and their reactive bonds is described and it is shown that these pathways can be obtained by conformational exploration with a chemically activating constraint.
Journal ArticleDOI
Negative ion Wolff rearrangement of some diazoketones: A theoretical mechanistic study
Ritu Arora,Rita Kakkar +1 more
TL;DR: The mechanism of the Wolff rearrangement of deprotonated diazocarbonyl compounds has been studied using density functional calculations, for both the gas and aqueous phases as discussed by the authors.
References
More filters
Journal ArticleDOI
409. The lupin alkaloids. Part VIII
Journal ArticleDOI
Dieckmann and thorpe reactions in dimethyl sulfoxide
Journal ArticleDOI
1-Methyl-3-ethyl-4-(p-hydroxyphenyl)-Δ3-cyclohexenylethyl carbinol, an “Open-Model” of Estradiol
Martin Rubin,Henry Wishinsky +1 more
Related Papers (5)
A Study of the Cyclization of a Series of ι,ι'-Dicarbethoxydialkylmethylamines through the Acetoacetic Ester Condensation
E. A. Prill,S. M. McElvain +1 more