Reactions of Aralkyl and Unsaturated Chloramines: The Nitrenium Ion Question

Abstract
Evidence for intermolecular electrophilic halogenation of aromatic rings and olefinic double bonds by aliphatic chloramines at low pH, and for homolytic cyclization of unsaturated chloramines in neutral medium is presented. Independent proof of structure and stereochemistry of derivatives of 6-azabicyclo[3.2.1]octane and 2-azabicyclo[2.2.2]octane was provided. No evidence for involvement of nitrenium ions in the chloramine reactions was observed.

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