The Stobbe reaction is a modification of this reaction specifically for diethyl succinate, which requires a weaker base to react. In reactions with ethyl esters, ethoxide is used as a base since nucleophilic acyl substitution occurs but will only result in formation of starting material. One equivalent of ethoxide catalyst is commonly added to the reaction mixture to drive the reaction toward the less stable products. This reaction requires the ester starting material to have at least two alpha-hydrogens, to account for the two ionization events that occur. An intramolecular analog of this reaction is known as the Dieckmann condensation, forming a cyclic beta-keto ester from a diester. FTP, identify this eponymous base-promoted condensation
The Stobbe reaction is a modification of this reaction specifically for diethyl succinate, which requires a weaker base to react. In reactions with ethyl esters, ethoxide is used as a base since nucleophilic acyl substitution occurs but will only result in formation of starting material. One equivalent of ethoxide catalyst is commonly added to the reaction mixture to drive the reaction toward the less stable products. This reaction requires the ester starting material to have at least two alpha-hydrogens, to account for the two ionization events that occur. An intramolecular analog of this reaction is known as the Dieckmann condensation, forming a cyclic beta-keto ester from a diester. FTP, identify this eponymous base-promoted condensation of two ester molecules to give a beta-keto ester.
The Stobbe reaction is a modification of this reaction specifically for diethyl succinate, which requires a weaker base to react.