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Formation of Eight-Membered Ring β-Keto Lactones Via the Intramolecular Trapping of Hydroxy Acylketenes‡

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Eight-membered ring β-keto lactones were prepared from 2,2,6-trimethyl-4H-1,3-dioxin-4-one in three steps involving conjugate addition to α,β-unsaturated aldehydes or ketones, followed by conversion to an alcohol and thermolysis. The formation of these eight-membered rings involves the intramolecular trapping of a hydroxy acyl ketene intermediate and is facilitated by a suppressed ring strain and an unfavorable intramolecular hydrogen bond, which is suggested to favor the formation of oligomers. These aspects of the reaction were supported by molecular mechanics calculations.

Affiliations: 1: Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661 U.S.A


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