Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation

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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Published in:Australian Journal of Chemistry
Main Author: Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
Format: Article
Language:English
Published: 2008
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-53849129584&doi=10.1071%2fCH08084&partnerID=40&md5=9d8786e8a067297b8d4340068539d580
id 2-s2.0-53849129584
spelling 2-s2.0-53849129584
Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation
2008
Australian Journal of Chemistry
61
10
10.1071/CH08084
https://www.scopus.com/inward/record.uri?eid=2-s2.0-53849129584&doi=10.1071%2fCH08084&partnerID=40&md5=9d8786e8a067297b8d4340068539d580
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 2008.

00049425
English
Article
All Open Access; Green Open Access
author Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
spellingShingle Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation
author_facet Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
author_sort Saha K.; Lajis N.H.; Abas F.; Naji N.A.; Hamzah A.S.; Shaari K.
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
publishDate 2008
container_title Australian Journal of Chemistry
container_volume 61
container_issue 10
doi_str_mv 10.1071/CH08084
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-53849129584&doi=10.1071%2fCH08084&partnerID=40&md5=9d8786e8a067297b8d4340068539d580
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. © CSIRO 2008.
publisher
issn 00049425
language English
format Article
accesstype All Open Access; Green Open Access
record_format scopus
collection Scopus
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