320-16-1Relevant articles and documents
Reaction of (E)-O-Arylbenzaldoximes with Sodium Methoxide in Methanol. Effect of Leaving Group upon Nitrile-Forming Transition State
Cho, Bong Rae,Jung, Jinhee,Ahn, Eun Kyung
, p. 3425 - 3429 (2007/10/02)
Reactions of (E)-O-arylbenzaldoximes 1-3 with MeONa-MeOH have been studied kinetically.The reactions proceed via competing E2 and SNAr reactions, in which the first step is rate-determining.Although the reactions were strongly influenced by the electronic effect of the β- and O-aryl substituents, they were insensitive to the steric effect of the O-aryl group, except that the SNAr reaction was retarded by the CF3 group of 2.For eliminations from 1-3 promoted by MeONa-MeOH, the kH/kD value increased and the Hammett ρ value decreased with better leaving groups.From these results, the effect of leaving group variation upon the nitrile-forming transition state is assessed.