Abstract
The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 411-420 |
| Number of pages | 10 |
| Journal | Journal of Organometallic Chemistry |
| Volume | 409 |
| Issue number | 3 |
| DOIs | |
| State | Published - Jun 4 1991 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry
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Cite this
Silverberg, L. J., Wu, G., Rheingold, A. L., & Heck, R. F. (1991). Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes. Journal of Organometallic Chemistry, 409(3), 411-420. https://doi.org/10.1016/0022-328X(91)80026-G