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 |
| Publication status | Published - 1996 |
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Keywords
- Benzo[g]cyclopenta[a]phenanthrenes
- Benzo[g]indeno[a]phenanthrenones
- Synthesis
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Short synthetic approach to benzo[g]cyclopenta[a]-phenanthrenes and benzo[g]-indeno[a]phenanthrenones. / Gács-Baitz, E.; Minuti, Lucio; Taticchi, Aldo.
In: Polycyclic Aromatic Compounds, Vol. 8, No. 4, 1996, p. 213-227.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Short synthetic approach to benzo[g]cyclopenta[a]-phenanthrenes and benzo[g]-indeno[a]phenanthrenones
AU - Gács-Baitz, E.
AU - Minuti, Lucio
AU - Taticchi, Aldo
PY - 1996
Y1 - 1996
N2 - 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.
AB - 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.
KW - Benzo[g]cyclopenta[a]phenanthrenes
KW - Benzo[g]indeno[a]phenanthrenones
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=0030503576&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030503576&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0030503576
VL - 8
SP - 213
EP - 227
JO - Polycyclic Aromatic Compounds
JF - Polycyclic Aromatic Compounds
SN - 1040-6638
IS - 4
ER -