Abstract
The synthesis of 3-vinyl-phenanthrene and 4-vinyl-1, 2-dihydro-phenanthrene is reported. High pressure Lewis acid-catalyzed cycloaddition reactions of both dienes with 4-acetoxy-2-cyclopenten-1-one are discussed. Whereas 4-vinyl-1, 2-dihydro-phenanthrene underwent the expected Diels-Alder reaction, 3-vinyl-phenanthrene underwent a [2π + 2π] cycloaddition. Both cycloadditions are totally regioselective. Structure analysis of the reaction products by 1H and 13C NMR spectroscopy is reported.
| Original language | English |
|---|---|
| Pages (from-to) | 213-227 |
| Number of pages | 15 |
| Journal | Polycyclic Aromatic Compounds |
| Volume | 8 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Jan 1 1996 |
Keywords
- Benzo[g]cyclopenta[a]phenanthrenes
- Benzo[g]indeno[a]phenanthrenones
- Synthesis
ASJC Scopus subject areas
- Polymers and Plastics
- Organic Chemistry
- Materials Chemistry
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Cite this
Gacs-Baitz, E., Minuti, L., & Taticchi, A. (1996). Short synthetic approach to benzo[g]cyclopenta[a]-phenanthrenes and benzo[g]-indeno[a]phenanthrenones. Polycyclic Aromatic Compounds, 8(4), 213-227. https://doi.org/10.1080/10406639608048349