
Journal of Organic Chemistry p. 2011 - 2015 (1988)
Update date:2022-08-29
Topics:
Roussis, Vassilios
Gloer, Katherine B.
Wiemer, David F.
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.
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