Regioselective friedel-crafts acetylations of 2-acetylanthracene

Tahani Mala'bi; Sergey Pogodin; Israel Agranat

doi:10.2174/1570178612666150218203612

Regioselective friedel-crafts acetylations of 2-acetylanthracene

Tahani Mala'bi
, Sergey Pogodin
, Israel Agranat^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

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.

Original language	English
Pages (from-to)	324-331
Number of pages	8
Journal	Letters in Organic Chemistry
Volume	12
Issue number	5
DOIs	https://doi.org/10.2174/1570178612666150218203612
State	Published - 2015

Bibliographical note

Publisher Copyright:
© 2015 Bentham Science Publishers.

Keywords

Acyl rearrangement
DFT
Friedel-crafts acylation
Kinetic control
Regioselectivity
Thermodynamic control

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@article{946113a8582449d6bdc5549e030c8f36,

title = "Regioselective friedel-crafts acetylations of 2-acetylanthracene",

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",

author = "Tahani Mala'bi and Sergey Pogodin and Israel Agranat",

note = "Publisher Copyright: {\textcopyright} 2015 Bentham Science Publishers.",

year = "2015",

doi = "10.2174/1570178612666150218203612",

language = "אנגלית",

volume = "12",

pages = "324--331",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers",

number = "5",

}

TY - JOUR

T1 - Regioselective friedel-crafts acetylations of 2-acetylanthracene

AU - Mala'bi, Tahani

AU - Pogodin, Sergey

AU - Agranat, Israel

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 - https://www.scopus.com/pages/publications/84931269417

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 -

Regioselective friedel-crafts acetylations of 2-acetylanthracene

Abstract

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Keywords

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