Abstract
The study of Friedel-Crafts acetylation of phenanthrente with acetic acid in polyphosphoric acid, along with re-arrangements and deacetylations of acetylphenanthrene isomers, indicated its reversibility. The structures of (E)-2-AcPHN and (Z)-9-AcPHN were determined by X-ray crystallography. PM3 calculations predicted that 9-AcPHN is the kinetically controlled while 2-AcPHN and 3-AcPHN are the thermodynamically controlled products, in accordance with experiment. The mutual rearrangements of 2-AcPHN and 9-AcPHN are noted.
| Original language | English |
|---|---|
| Pages (from-to) | 314-318 |
| Number of pages | 5 |
| Journal | Letters in Organic Chemistry |
| Volume | 4 |
| Issue number | 5 |
| DOIs | |
| State | Published - Jul 2007 |
Keywords
- Agranat-Gore rearrangement
- Deacylation
- Overcrowding
- PM3 calculations
- PPA
- X-ray crystallography
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