Steric effects in the base-catalysed conversion of 2-cyanophenyl 2,4,6-tri-t-butylbenzoate into 2,4,6-tri-t-butylbenzonitrile in aqueous alcohol

Abstract

That conditions appropriate for the hydration of a nitrile to an amide are also appropriate for the reverse dehydration of an amide to an nitrile is demonstrated in the base-catalysed conversion of 2-cyanophenyl 2,4,6-tri-t-butylbenzoate into 2,4,6-tri-t-butylbenzonitrile and salicylic acid via amide intermediates, the equilibria between amide and nitrile being determined in Part by The steric environment of the groups concerned.