| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5278318 | Tetrahedron Letters | 2011 | 4 Pages |
Abstract
1,5-, 1,8- and 9,10-diacetylanthracenes undergo Friedel-Crafts acyl rearrangements in polyphosphoric acid at 130-150 °C to give 3-methylbenz[de]anthracen-1-one via the kinetically-controlled 1,9-diacetylanthracene. The rearrangement mechanism is supported by DFT calculations of diacetylanthracenes, their Ï-complexes, O-protonates, and O,O-diprotonates. The importance of kinetic control versus thermodynamic control in Friedel-Crafts acyl rearrangements is highlighted. Certain features of reversibility are also suggested.
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Authors
Tahani Mala'bi, Sergey Pogodin, Israel Agranat,