Journal of the Chemical Society. Perkin transactions II p. 775 - 780 (1984)
Update date:2022-08-10
Topics:
Cacace, Fulvio
Ciranni, Giovanna
Marzio, Annito Di
The isomerization of bromoxylenes following protonation by X3+ (X=H or D), CnH5+ (n=1 or 2), iso-C3H7+, and t-C4H9+ ions in the dilute gas state has been investigated.Further evidence has been derived from chemical ionization mass spectrometry and related radiolytic experiments concerning methylation of bromotoluenes by gaseous (CH3)2F+ ions.The results suggest that the observed intramolecular Br migration involves the intermediacy of a radical cation-bromine atom pair.The mechanistic relevance of the results to gas-phase aromatic substitution by free bromine cations is discussed.
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