Journal article
Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones
Journal of organic chemistry, Vol.57(1), pp.317-321
01/01/1992
DOI: 10.1021/jo00027a055
Abstract
Diethyl vinyl phosphates derived from simple alkyl-substituted cyclohexanones and cyclohexenones are known to rearrange to β-keto phosphorates upon treatment with excess LDA. To establish the effect of oxygen-containing functional groups on this transformation, vinyl phosphates containing remote carbonyl groups or acetals have been studied. The rearrangement fails in the presence of unprotected carbonyl groups but proceeds in the presence of acetals. To establish the regiochemistry of this rearrangement in fused-ring systems, representative decalins were studied. Through use of various ketones and enones, the 2- and 4-phosphono 3-keto compounds have been prepared in both cis- and trans-fused decalin series. © 1992, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones
- Creators
- Yi Zhong AnDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.57(1), pp.317-321
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00027a055
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 01/01/1992
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216568902771
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