Journal article
A skeletal rearrangement of .gamma.-(acyloxy)-.beta.-keto phosphonates: studies on the formation of 2(3H)-furanones
Journal of organic chemistry, Vol.53(9), pp.2011-2015
04/01/1988
DOI: 10.1021/jo00244a031
Abstract
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. © 1988, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- A skeletal rearrangement of .gamma.-(acyloxy)-.beta.-keto phosphonates: studies on the formation of 2(3H)-furanones
- Creators
- Vassilios RoussisKatherine B GloerDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.53(9), pp.2011-2015
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00244a031
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 04/01/1988
- Academic Unit
- Chemistry; Neuroscience and Pharmacology
- Record Identifier
- 9984217456202771
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