TY - JOUR
T1 - Regioselective friedel-crafts acetylations of 2-acetylanthracene
AU - Mala'bi, Tahani
AU - Pogodin, Sergey
AU - Agranat, Israel
N1 - Publisher Copyright:
© 2015 Bentham Science Publishers.
PY - 2015
Y1 - 2015
N2 - 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.
AB - 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.
KW - Acyl rearrangement
KW - DFT
KW - Friedel-crafts acylation
KW - Kinetic control
KW - Regioselectivity
KW - Thermodynamic control
UR - http://www.scopus.com/inward/record.url?scp=84931269417&partnerID=8YFLogxK
U2 - 10.2174/1570178612666150218203612
DO - 10.2174/1570178612666150218203612
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AN - SCOPUS:84931269417
SN - 1570-1786
VL - 12
SP - 324
EP - 331
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 5
ER -