Claisen condensation and Dieckmann cyclization

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Information about Claisen condensation and Dieckmann cyclization
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Published on March 7, 2014

Author: AshitoshLokhande

Source: slideshare.net

Description

oraganic Msc Part I

Claisen Condensation and Dieckmann Cyclization By- Aashitosh Solanki MSc Part I AA8

Claisen Condensation Principle : When an ester molecule undergoes nucleophilic acyl substitution by an enolate. The intermediate has an alkoxy (―OR) group that act as a leaving group, leaving a β-keto ester. The overall reaction 2 ester molecules to give β-keto ester.

General Reaction : Example:

Mechanism Formation of Enolate ion Addition of enolate ion Elimination of alkoxy group

Application

Dieckmann Cyclisation Principle: The intermolecular Claisen condensation of 1,6 and 1,7 diesters undergo strongly basic conditions to form cyclic β – keto ester is known as Dieckmann Cyclisation. A 1,6-diester gives a 5 membered ring. A 1,7-diester gives a 6 membered ring.

General Reaction Example :

Mechanism

Application 1. 2.

Walter Dieckmann (1869-1925) Ludwig Claisen (1851-1930)

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