Ambident (chemistry)

In chemistry, ambident is a molecule or group that has two alternative and interacting reaction sites, to either of which a bond may be made during a reaction.

Ambident dienophile
Ambident dienophile 57 reacts with DAPC 54 at the cyclobutene π-bond to produce ligand 58; in contrast, the related ambident dienophile 59 reacts with DAPC 54 at the naphthoquinone π-center to produce adduct 60 (lack of shielding of the methylene protons supports the stereochemical assignment).

Ambident Nucleophile
An Ambident nucleophile refers to an anionic nucleophile that exhibits resonance delocalization of its negative charge over two unlike atoms or over two like but non-equivalent atoms. Enolate ions are Ambident Nucleophile.