Investigation of the Mechanism for the Preparation of 6-Phenyl-2, 4-dioxotetrahydropyrans by the Potassium Carbonate Promoted Condensation between …

B Andersh, ET Nguyen, RJ Van Hoveln…

Index: Andersh, Brad; Nguyen, Elizabeth T.; Van Hoveln, Ryan J.; Kemmerer, Dylan K.; Baudo, David A.; Graves, Jessica A.; Roark, Mollie E.; Bosma, Wayne B. Journal of Organic Chemistry, 2013 , vol. 78, # 9 p. 4563 - 4567

Full Text: HTML

Citation Number: 3

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, 1H NMR monitoring studies, and reactivity studies, our proposed mechanism for this reaction involves deprotonation at the ...