Acyl - Acylium Cations, Anions, and Radicals

Acylium Cations, Anions, and Radicals

Acylium ions are cations of the formula RCO+. The oxygen and carbon are linked by a triple bond. Such species are common reactive intermediates, for example, in the Friedel-Crafts acylations also in many other organic reactions such as the Hayashi rearrangement. Salts containing acylium ions can be generated by removal of the halide from acyl halides:

RC(O)Cl + SbCl5 → SbCl6

The C-O distance in these cations is near 1.1 angstrom, even shorter than that in carbon monoxide. Acylium cations are characteristic fragments observed in EI-mass spectra of ketones.

Acyl anions and acyl radicals are very rare. Organolithium compounds with Li-C(O)R linkages are not well studied.

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