text: The canonical umpolung reagent is the cyanide ion. The cyanide ion is unusual in that a carbon triply bonded to a nitrogen would be expected to have a (+) polarity due to the higher electronegativity of the nitrogen atom. Yet, the negative charge of the cyanide ion is localized on the carbon, giving it a (-) formal charge. This chemical ambivalence results in umpolung in many reactions where cyanide is involved.
  For example, cyanide is a key catalyst in the benzoin condensation, a classical example of polarity inversion.
  The net result of the benzoin reaction is that a bond has been formed between two carbons that are normally electrophiles.