Steric effects of polymethylcarboranes. Unusual reactivity of N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium

  • Yaguchi K
  • Endo Y
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Reaction of deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl chloride with aniline in pyridine gives predominantly deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carboxamide, accompanied by a small amount of the expected anilide. The results may be interpreted in terms of nucleophilic attack of aniline at the 2'-position of the N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium intermediate, followed by ring-opening of the pyridine nucleus and recyclization.

Author-supplied keywords

  • Carboranes
  • Pyridinium salts
  • Reissert compounds
  • Steric effect
  • Strain effect

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  • Kyoko Yaguchi

  • Yasuyuki Endo

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