Reactions with Aromatic Compounds of Recoiling Bromine Atoms Formed from the 76,77Kr –* 76,77Br Transformations. Liquid-Phase Reactions

Stephen M. Moerlein, Michael J. Welch, Alfred P. Wolf

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Abstract

Bromine atoms produced via the 76Kr(EC)76Br and 77Kr(β+/EC)77Br transformations were reacted with simple benzenoid compounds in the liquid phase. For both 76Kr and 77Kr, bromodeprotonation resulted in a reactivity constant p+⋍ -0.6, with higher yields for 76Br. Whereas bromodeprotonation was hypothesized to occur via formation of a product-determining σ-complex by radical bromine species, ipso substitution was described in terms of a two-step addition-elimination mechanism in which bond breakage is product determining. While radical bromine species are probably involved in substituent displacements from monosubstituted arenes, polysubstituted aromatic compounds activated to nucleophilic attack were shown to involve an additional nucleophilic reaction pathway.

Original languageEnglish
Pages (from-to)5418-5428
Number of pages11
JournalJournal of the American Chemical Society
Volume105
Issue number16
DOIs
StatePublished - Aug 1983

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