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Effects of structured solids on regioselectivity of dibromination of naphthalene

Smith, Keith, Al-Khalaf, Alaa K. H., Berkil Akar, Kıymet, Al-Badri, Doaa J. K., Kariuki, Benson M. and El-Hiti, Gamal A. 2021. Effects of structured solids on regioselectivity of dibromination of naphthalene. Catalysts 11 (5) , 540. 10.3390/catal11050540

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Abstract

The influence of structured solids (amorphous, lamellar and 3D crystalline) on the regioselectivity of the dibromination of naphthalene using bromine at room temperature has been investigated. The more acidic amorphous catalysts and an acidic clay give rapid reactions and lead to a large preponderance of 1,4-dibromonaphthalene over the 1,5-dibromo compound, while calcined KSF clay, a bentonite material, after a short reaction time gives a small predominance of the 1,5-isomer. Longer reaction times lead to the equilibration of reaction mixtures, which means that the 1,4-isomer eventually predominates in all cases. Based on these observations, it has been possible to devise synthetically useful preparative procedures, involving direct room temperature reactions of bromine with naphthalene, for either 1,4-dibromonaphthalene or 1,5-dibromonaphthalene based on the use of different solids, namely Synclyst 13 and KSF clay, respectively.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: MDPI
ISSN: 2073-4344
Date of First Compliant Deposit: 6 May 2021
Date of Acceptance: 21 April 2021
Last Modified: 07 May 2021 14:00
URI: https://orca.cardiff.ac.uk/id/eprint/140981

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