10208-16-9Relevant academic research and scientific papers
Reversible Friedel-Crafts acylations of anthracene: Rearrangements of acetylanthracenes
Mala'bi, Tahani,Pogodin, Sergey,Agranat, Israel
, p. 237 - 241 (2009)
Treatment of 1-acetylanthracene (1-AcAN) and 9-acetylanthracene (9-AcAN) with PPA at 80-120 °C leads to the nearly complete conversion of these isomers into 2-acetylanthracene (2-AcAN), an illustration of the Agranat-Gore rearrangement of polycyclic aromatic ketones (PAKs). Ab initio MP2/6-31(d) calculations predict the following order of stabilities: for O-complexes: 9-AcAN>1-AcAN>2-AcAN; for ketones: 2-AcAN>1-AcAN>9-AcAN; for O-protonated ketones: 2-AcAN>1-AcAN>9-AcAN. Thus, 9-AcAN is the kinetically controlled product, whereas 2-AcAN is the thermodynamically controlled product. No reverse rearrangements of 2-AcAN to either 9-AcAN or 1-AcAN and of 1-AcAN to 9-AcAN were observed. The results strengthen the pattern of reversibility in Friedel-Crafts acylations of PAHs.
Kinetic control wins out over thermodynamic control in Friedel-Crafts acyl rearrangements
Mala'bi, Tahani,Pogodin, Sergey,Agranat, Israel
scheme or table, p. 1854 - 1857 (2011/04/26)
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.
Friedel-Crafts reactions in room temperature ionic liquids
Adams, Christopher J.,Earle, Martyn J.,Roberts, Glyn,Seddon, Kenneth R.
, p. 2097 - 2098 (2007/10/03)
Friedel-Crafts reactions in the ionic liquid system 1-methyl-3-ethylimidazolium chloride-aluminium(III) chloride can be performed with excellent yields and selectivities, and in the case of anthracene, have been found to be reversible.
