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Nitrile-forming eliminations from (1) promoted by in 70 mol % MeCN(aq) have been studied kinetically. When X = , the reactions exhibited second-order kinetics as well as Brnsted = 0.63 and = 0.34-0.46, and an E2 mechanism is evident. As the leaving group was made poorer (X = H, Cl, and ), Brnsted value increased from 0.63 to 0.85-0.89 without much change in the value E2, indicating that structure of the transition state changed to an E1cb-like with extensive bond cleavage, significant negative charge development at the -carbon, and limited -OAr bond cleavage.

bulletin of the korean chemical society

Elimination Reactions of (E)-2,4,6-Trinitrobenzaldehyde O-Aryloximes Promoted by R3N/R3NH+in 70 mol% MeCN(aq). Effect of β-Aryl Group the Nitrile-Forming Transition-State