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Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation

Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distrib...

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Main Authors: Koushik, Saha, Lajis, Md Nordin, Abas, Faridah, Ali Naji, Nabil, Hamzah, A. Sazali, Shaari, Khozirah
Format: Article
Language:English
English
Published: CSIRO Publishing 2008
Online Access:http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf
http://psasir.upm.edu.my/id/eprint/6021/
http://dx.doi.org/10.1071/CH08084
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spelling my.upm.eprints.60212015-09-28T07:56:10Z http://psasir.upm.edu.my/id/eprint/6021/ Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation Koushik, Saha Lajis, Md Nordin Abas, Faridah Ali Naji, Nabil Hamzah, A. Sazali Shaari, Khozirah Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all. CSIRO Publishing 2008 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf Koushik, Saha and Lajis, Md Nordin and Abas, Faridah and Ali Naji, Nabil and Hamzah, A. Sazali and Shaari, Khozirah (2008) Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation. Australian Journal of Chemistry, 61 (10). pp. 821-825. ISSN 0004-9425 http://dx.doi.org/10.1071/CH08084 10.1071/CH08084 English
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
English
description Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all.
format Article
author Koushik, Saha
Lajis, Md Nordin
Abas, Faridah
Ali Naji, Nabil
Hamzah, A. Sazali
Shaari, Khozirah
spellingShingle Koushik, Saha
Lajis, Md Nordin
Abas, Faridah
Ali Naji, Nabil
Hamzah, A. Sazali
Shaari, Khozirah
Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
author_facet Koushik, Saha
Lajis, Md Nordin
Abas, Faridah
Ali Naji, Nabil
Hamzah, A. Sazali
Shaari, Khozirah
author_sort Koushik, Saha
title Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
title_short Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
title_full Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
title_fullStr Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
title_full_unstemmed Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
title_sort halophenol rearrangement in lewis acid-catalyzed friedel–crafts conditions: evidence of competitive initial protonation and acylation
publisher CSIRO Publishing
publishDate 2008
url http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf
http://psasir.upm.edu.my/id/eprint/6021/
http://dx.doi.org/10.1071/CH08084
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score 13.211869

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