Rearrangement of α-Aminoketones During Clemmensen Reduction. III. Contraction of a Seven-membered Ring in the Monocyclic Series

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.

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Azepanes (Hexahydroazepines)

1997

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Rearrangement of α-Aminoketones During Clemmensen Reduction. III. Contraction of a Seven-membered Ring in the Monocyclic Series

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Zinc Amalgam

Zinc Amalgam

TheDieckmann Condensation (Including theThorpe‐Ziegler Condensation)

Azepanes (Hexahydroazepines)

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