Dieckmann Condensation - Reaction, Mechanism, and Examples

Dieckmann Condensation - Reaction, Mechanism, and Examples are described in this article.

Dieckmann condensation is a chemical reaction for the synthesis of cyclic β-keto esters. In this reaction diester reacts with base to produce cyclic β-keto esters. It is a Named reaction in organic chemistry.

Key words: Condensation, Cyclization reaction, β-keto esters, Named reaction.

Introduction

The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give cyclic β-keto esters. The equivalent intermolecular reaction is the Claisen condensation. This is a ring forming or cyclization reaction. This organic reaction named after the German chemist Walter Dieckmann (1869–1925).

Figure : 1 Dieckmann Condensation

Mechanism

The mechanism of Dieckmann condensation consists of three steps;

Step 1: Proton abstraction by strong base to form enolate ion.

Step 2: Nucleophilic addition of enolate ion on carbonyl carbon.

Step 3: Elimination of alkoxide ion to produce cyclic β-keto ester.

Figure : 2 Mechanism of Dieckmann Condensation 

Examples:

Figure : 3 Examples of Dieckmann Condensation 

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