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 σ-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.
Original language | English |
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Pages (from-to) | 1854-1857 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 16 |
DOIs | |
State | Published - 20 Apr 2011 |
Keywords
- DFT calculations
- Diacetylanthracenes
- Polyphosphoric acid
- Rearrangement mechanism
- Reversibility