Journal article
Synthesis of .alpha.-phosphono lactones and esters through a vinyl phosphate-phosphonate rearrangement
Journal of organic chemistry, Vol.54(20), pp.4750-4754
09/01/1989
DOI: 10.1021/jo00281a012
Abstract
Upon treatment with base, the diethyl vinyl phosphate derivatives of five-, six-, and seven-membered-ring lactones undergo rearrangement to a-phosphono lactones in very good yields. Because the vinyl phosphates can be prepared in situ, these a-phosphono lactones can be obtained from the parent lactones in a one-flask protocol, making this methodology a convenient alternative to the traditional Arbuzov synthesis. An analogous reaction sequence can be used to prepare some a-phosphono esters, but yields are generally lower and the rearrangement becomes minimal with esters hindered at the β-position. © 1989, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Synthesis of .alpha.-phosphono lactones and esters through a vinyl phosphate-phosphonate rearrangement
- Creators
- John A JacksonGerald B HammondDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.54(20), pp.4750-4754
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00281a012
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 09/01/1989
- Academic Unit
- Chemistry; Neuroscience and Pharmacology
- Record Identifier
- 9984216608602771
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