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Preparation of Vinylcyclopropanes by Sodium Mediated Reductive Isomerization of Methylenecyclopropanes.
- Source :
-
Journal of Organic Chemistry . 9/4/2015, Vol. 80 Issue 17, p8821-8829. 9p. - Publication Year :
- 2015
-
Abstract
- We disclosed therein a new reaction of reductive isomerization of methylenecyclopropanes (MCPs) to vinylcyclopropanes (VCPs). On treatment with sodium metal in liquid ammonia, MCPs bearing a C-O bond at allylic position undergo both a reductive cleavage of the C-O bond and an isomerization of the C-C double bond giving rise to VCPs. The scope of the reductive isomerization was investigated and showed a broad applicability since various functional groups are tolerated. MCP substrates were straightforwardly prepared by a palladium-promoted [2 + 1] cycloaddition between norbornene derivatives with alkynes. [ABSTRACT FROM AUTHOR]
- Subjects :
- *VINYLCYCLOPROPANES
*CYCLOPROPANE
*SODIUM
*ALKALI metals
*ISOMERIZATION
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 80
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 109564094
- Full Text :
- https://doi.org/10.1021/acs.joc.5b01205