title: Investigation of the mechanism for the preparation of 6-phenyl-2,4-dioxotetrahydropyrans by the potassium carbonate promoted condensation between acetoacetate esters and benzaldehyde.
abstract: Treatment of benzaldehyde and an acetoacetate ester with potassium carbonate in an alcohol solvent proceeds via γ-C-alkylation rather than α-C-alkylation resulting in the formation of 6-phenyl-2,4-dioxotetrahydropyran. Based upon results from deuterium exchange experiments, carbon-13 labeling experiments, (1)H NMR monitoring studies, and reactivity studies, our proposed mechanism for this reaction involves deprotonation at the α-carbon, intramolecular proton transfer to form a γ-anion, addition of the resulting γ-anion to the carbonyl carbon of benzaldehyde, and intramolecular transesterification.
authors.affiliation: Mund-Lagowski Department of Chemistry and Biochemistry, Bradley University, Peoria, Illinois 61625, United States. bja@bradley.edu
authors.forename: Brad
authors.initials: B
authors.lastname: Andersh
authors.forename: Elizabeth T
authors.initials: ET
authors.lastname: Nguyen
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Van Hoveln
authors.forename: Dylan K
authors.initials: DK
authors.lastname: Kemmerer
authors.forename: David A
authors.initials: DA
authors.lastname: Baudo
authors.forename: Jessica A
authors.initials: JA
authors.lastname: Graves
authors.forename: Mollie E
authors.initials: ME
authors.lastname: Roark
authors.forename: Wayne B
authors.initials: WB
authors.lastname: Bosma