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Dialkyl chloronium ions

  • Author(s): Stoyanov, ES
  • Stoyanova, IV
  • Tham, FS
  • Reed, CA
  • et al.

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(Figure Presented) The carborane acid H(CHB11Cl11) reacts with chloroalkanes RCl to give is olable dialkylchloronium ion salts, [R2Cl][CHB11Cl11], that are stable at room temperature. X-ray crystal structures have been obtained for R = CH3and CH2CH3, revealing bent cation structures with C-Cl-C angles of 101.5 and 105.8°, respectively. The dimethylchloronium ion salt loses CH3Cl upon heating and forms sublimable CH3(CHB11Cl11), providing a clean synthetic route to an extremely potent electrophilic methylating agent. IR spectra of all species have been interpreted, including the C-Cl stretch in CH3-ClCHB11Cl10. Copyright © 2010 American Chemical Society.

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