Regioselective Friedel-Crafts Acetylations of 2-Acetylanthracene

Title:Regioselective Friedel-Crafts Acetylations of 2-Acetylanthracene

Volume: 12 Issue: 5

Author(s): Tahani Mala'bi, Sergey Pogodin and Israel Agranat

Affiliation:

Keywords: Acyl rearrangement, DFT, friedel-crafts acylation, kinetic control, regioselectivity, thermodynamic control.

Abstract: The Friedel-Crafts acetylation of 2-acetylanthracene (2-AcAN) with AcCl and AlCl₃ in 1,2-C₂H₄Cl₂ gave a mixture of 1,6-diacetylanthracene (1,6-Ac₂AN) and 1,7-diacetylanthracene (1,7-Ac₂AN), while the Friedel-Crafts acetylation of 2-AcAN in nitrobenzene gave 2,7-diacetylanthracene (2,7-Ac₂AN). Both reactions were highly regioselective. B3LYP/6-31G(d) calculations of diacetylanthracenes, their O-protonates and their σ-complexes indicate that 1,6-Ac₂AN and 1,7-Ac₂AN are the kinetically controlled products, whereas, 2,7-Ac₂AN is the thermodynamically controlled product.

Cite this article as:

Mala'bi Tahani, Pogodin Sergey and Agranat Israel, Regioselective Friedel-Crafts Acetylations of 2-Acetylanthracene, Letters in Organic Chemistry 2015; 12 (5) . https://dx.doi.org/10.2174/1570178612666150218203612