Article Kinetics and Mechanism of Bromination of Toluene and Substituted Toluenes by N-Bromo Acetamide (NBA) was published on January 1, 1987 in the journal Zeitschrift für Physikalische Chemie (volume 268O, issue 1).

AbstractThe kinetics of chlorination of toluene, o‐methyl toluene, p‐methyl toluene, m‐methyl toluene, and m‐chlorotoluene by chloramine‐T(CAT) in aqueous acetic acid in the presence of HClO4 have been studied. The reaction is first order with respect to [CAT] as well as [H+]. The order with respect to the substrate is unity in the case of toluene and m‐chlorotoluene, fractional in the case of o‐methyl toluene and p‐methyl toluene, and zero order in the case of m‐methyl toluene. Nuclear halogenation has been observed with m‐methyl toluene, while nuclear and side‐chain halogenation for p‐methyl toluene and o‐methyl toluene, and sidechain halogenation for toluene and m‐chlorotoluene are the pathways. An increase in the proportion of acetic acid accelerates the rate. Added acetate ions inhibit the reaction, and added p‐toluene sulfonamide causes a pronounced retardation. A mechanism involving AcO+HCl as the important electrophile is discussed.

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Chemischer InformationsdienstVolume 10, Issue 38 Preparative Organic Chemistry ChemInform Abstract: KINETICS AND MECHANISM OF OXIDATION OF CYCLOPENTANONE, CYCLOHEXANONE, CYCLOHEPTANONE AND CYCLOOCTANONE BY PHENYL IODOSOACETATE S. C. PATI, S. C. PATISearch for more papers by this authorB. R. DEV, B. R. DEVSearch for more papers by this author S. C. PATI, S. C. PATISearch for more papers by this authorB. R. DEV, B. R. DEVSearch for more papers by this author First published: September 18, 1979 https://doi.org/10.1002/chin.197938149AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume10, Issue38September 18, 1979 RelatedInformation