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

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

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Official URL: http://dx.doi.org/10.1071/CH08084

Abstract

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.

Item Type:Article
Faculty or Institute:Faculty of Science
Publisher:CSIRO Publishing
DOI Number:10.1071/CH08084
Altmetrics:http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1071/CH08084
ID Code:6021
Deposited By: Najwani Amir Sariffudin
Deposited On:07 May 2010 15:26
Last Modified:20 Jul 2010 15:31

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