Reactions of Cation Radicals of EE Systems. III. Chlorination of 9,10-Diphenylanthracene

John F. Evans, Henry N. Blount

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Stopped-flow kinetic studies of the reaction of 9,10-diphenylanthracene (DPA) cation radical (DPA·+) with chloride ion in acetonitrile gives rise to a rate law which is second order in DPA·+, first order in Cl, and independent of DPA. The product of the reaction of electrogenerated DPA·+ with Cl was shown to be 9,10-dichloro-9,10-diphenyl-9,10-dihydroanthracene (1), which undergoes both surface catalyzed and thermally induced rearrangement to 2-chloro-DPA (2) via loss of HCl. The mechanism proposed for the addition of Cl to DPA·+ to form 1 involves an associative equilibrium and is of a form which accounts for the observed kinetics as well as those previously reported for the hydroxylation and pyridination of DPA·+, which followed a different rate law.

Original languageEnglish (US)
Pages (from-to)516-519
Number of pages4
JournalJournal of Organic Chemistry
Issue number3
StatePublished - Feb 1 1976

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