Journal article
Mild, Zinc-Induced Defluorination of Butatrienes: Stereoselective Formation of Divinylacetylene Derivatives
Journal of organic chemistry, Vol.59(8), pp.2119-2121
04/01/1994
DOI: 10.1021/jo00087a030
Abstract
Defluorination of R(Ph)C═C═C(Ph)R[R=C2F5(3b); R = n-C3F7(3c)]was accomplished under remarkably mild conditions: Zn/rt/18 h. Reaction of pure (E)- or (Z)-3b with Zn gave in both instances 89-96% (E,E)-CF3CF═C(Ph)C≡CC(Ph)═CFCF3 in greater than 95% isomeric purity. The latter product was characterized by X-ray crystallography. Similarly, treatment of pure (E)- or (Z)-3c with Zn gave 70-93% CF3CF2CF═C(Ph)C≡CC(Ph)═CFCF2CF3 in 95% isomeric purity, although the stereochemistry could not be determined. A single electron transfer (SET) mechanism is proposed for the defluorination reaction.
Details
- Title: Subtitle
- Mild, Zinc-Induced Defluorination of Butatrienes: Stereoselective Formation of Divinylacetylene Derivatives
- Creators
- Peter A MorkenDonald J BurtonDale C Swenson
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.59(8), pp.2119-2121
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00087a030
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 04/01/1994
- Academic Unit
- Chemistry
- Record Identifier
- 9984622046802771
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