Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl

Lee, Kheng H. (1970) Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl. Tetrahedron, 26 (5). pp. 1503-1507. ISSN 0040-4020

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Official URL: https://doi.org/10.1016/S0040-4020(01)92979-5

Abstract

The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ constant was found to differ from the value (-0·74) previously reported for BrCCl3. Different selectivity values were obtained for I and BrCCl3 toward benzaldehyde, ethylbenzene, benzyl methyl ether, benzhydryl methyl ether, and benzyl benzhydryl ether. These results indicate that the CCl3SO2 radical is mainly responsible for benzylic hydrogen-abstraction. © 1970.

Item Type: Article
Additional Information: Lee, K.H.; Department of Chemistry, University of Malaya, Malaysia
Uncontrolled Keywords: Polar effects; hydrogen abstraction; benzaldehydes-II; radical chlorination
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Mr Jasny Razali
Date Deposited: 09 Mar 2021 00:49
Last Modified: 09 Mar 2021 00:49
URI: http://eprints.um.edu.my/id/eprint/24697

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