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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 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 07:26
Last Modified:20 Jul 2010 07:31

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