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Butenolide Synthesis Via Cation-Initiated Ring Expansion/Elimination Of Β-Lactones, Jianhua Huang
Butenolide Synthesis Via Cation-Initiated Ring Expansion/Elimination Of Β-Lactones, Jianhua Huang
Masters Theses
An area of recent research in the Black research group is an exploration of the potential of cation-initiated β-lactone ring expansions, accompanied by the elimination of a proton or other electrofuge, as a protocol for the synthesis of multisubstituted butenolides.
Γ-Bromo β-lactones were prepared via bromolactonization of the appropriate β,Γ-unsaturated acids under basic conditions. The nucleofugal bromine atom on the Γ-carbon was then employed to effect carbocation formation adjacent to the lactone ring oxygen atom; the most efficacious reagent combination was found to be silver nitrate in refluxing acetic acid. Generation of this cation initiated a migration of the β-lactone …