Diethyl ethanedioate

An important variation on the Claisen condensation is to use a ketone as the anionic reagent. This often works well because ketones usually are more acidic than simple esters and the base-induced self-condensation of ketones (aldol addition) is thermodynamically unfavorable (Section 17-3C). A typical example is the condensation of cyclohexanone with diethyl ethanedioate (diethyl oxalate) ... 

SYNS DIETHYL ETHANEDIOATE ETHYL OXALATE ETHYL OXALATE (DOT) OXALIC ACID, DIETHYL ESTER... 

Diethyl Oxalate, Ethanedioic acid diethyl ester ethyl oxalate diethyl ethanedio te oxalic acid diethyl ester. c[Pg.493]

Diethyl ethanedioate. See Diethyl oxalate Diethyl ethanephosphonate. See Diethyl ethylphosphonate... 

Synonyms Diethyl ester, oxalic acid Diethyl ethanedioate Ethanedioic acid diethyl ester Ethyl oxalate Oxalic acid, diethyl ester... 

Synthesis a is a Dieckmann condensation featuring attack of the a-carbon of the ketone enolate on the ester carbonyl at the other end of the molecule. S5mthesis fc is a mixed Claisen condensation in which cyclohexanone enolate attacks one of the two ester groups of diethyl ethanedioate (diethyl oxalate). 

Chehdonic acid, a4-oxacyclohexanone (common name, 7-pyrone), is found in a number of plants and is synthesized from acetone and diethyl ethanedioate. Formulate a mechanism for this transformation. 

Diethylenimide oxide. See Morpholine Diethyl ester, oxalic acid. See Diethyl oxalate N,N-Diethylethanamine. See Triethylamine Diethyl ethanedioate. See Diethyl oxalate 2,2-Diethyl ethanol. See 2-Ethyl-1-butanol... 

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