Journal of Radioanalytical and Nuclear Chemistry

, Volume 92, Issue 2, pp 357–362 | Cite as

Alkylation of benzyl chloride by gaseous carbenium ions

  • B. Aliprandi
  • F. Cacace


The alkylation of benzyl chloride has been studied in the gas phase using radiolytically formed carbenium ions as the charged reagents. The intramolecular selectivity of the electrophilic attack, deduced from the composition of the neutral products, is characterized by the comparable reactivity of the aromatic ring and of the halogen atom of the substrate toward the gaseous cations. As to ring alkylation, the reactivity of the ortho positions of benzyl chloride is considerably lower than those of chlorobenzene. The results are compared with pertinent mass-spectrometric data, and discussed in connection with existing models of gas phase aromatic substitution by charged electrophiles.


Benzyl Aromatic Ring Alkylation Halogen Chlorobenzene 
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Copyright information

© Akadémiai Kiadó 1985

Authors and Affiliations

  • B. Aliprandi
    • 1
  • F. Cacace
    • 1
  1. 1.Università di Roma “La Sapienza”Rome(Italy)

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