Named after Walter Dieckmann Organic Chemistry Portal dieckmann-condensation | Reaction type Ring forming reaction | |
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The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-ketoesters. It is named after the German chemist Walter Dieckmann (1869–1925). The equivalent intermolecular reaction is the Claisen condensation.
Reaction Mechanism
Deprotonation of an ester at the α-position generates an enolate ion which then undergoes a 5-exo-trig nucleophilic attack to give a cyclic enol. Protonation with a Brønsted-Lowry acid (H3O+ for example) re-forms the β-keto ester.
Owing to the steric stability of five- and six-membered ring structures, these will preferentially be formed. So 1,6 diesters will form five-membered cyclic β-keto esters, while 1,7 diesters will form six-membered β-keto esters.
References
Dieckmann condensation Wikipedia(Text) CC BY-SA