A Skeletal Rearrangement of γ-(Acyloxy)-β-keto Phosphonates: Studies on the Formation of 2(3H)-Furanones

Article abstract of DOI:10.1021/jo00244a031

When treated with sodium hydride in dimethoxyethane, some γ-(acyloxy)-β-keto phosphonates react to give 2(3H)-furanones via an unexpected rearrangement which proceeds with carbon-carbon bond formation.Several possible mechanisms for this transformation have been tested through crossover experiments, rearrangement of an isotopically labeled substrate, and synthesis of a model intermediate.Results from these experiments allow elimination of several potential reaction pathways from further consideration and suggest a focus for future studies.