Synthesis of alfa,alfa-diaryl nitriles by radical nucleophilic substitution

TEMPESTI, TOMAS C.; PIERINI, ADRIANA B.; BAUMGARTNER, M. T.

ROYAL SOC CHEMISTRY

Año: 2012 vol. 36 p. 597 - 597

he present study shows that the anion of 2-naphthylacetonitrile is substituted selectively at its Calfa by aromatic halides, through a radical nuclephilic substitution mechanism, to give the corresponding alfa,alfa-diaryl nitriles in good yields. The regioselectivity of this ambident nucleophile changes with the steric hindrance of the radical centre from the aromatic substrate. The selectivity observed was investigated through a computational model of the key reaction step.