Regioselective Friedel-Crafts Acetylations of 2-Acetylanthracene

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

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 5 , 2015

Become EABM
Become Reviewer

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.

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

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 12
ISSUE: 5
Year: 2015
Page: [324 - 331]
Pages: 8
DOI: 10.2174/1570178612666150218203612
Price: $65

Article Metrics

PDF: 32
HTML: 2
EPUB: 1
PRC: 1