A remarkable mechanistic dichotomy in the acid-catalysed decomposition of the N- and C-adducts of indolide anions with 1,3,5-trinitrobenzene

Decomposition of the N- and C-adducts of indolide anions with 1,3,5-trinitrobenzene is subject to specific acidcatalysis in the former case and general-acid-catalysis in the latter through an SEAr process.

[1]  R. Manderville,et al.  Ambident Reactivity of Enolate Ions toward 1,3,5-Trinitrobenzene. The First Observation of an Oxygen-Bonded Enolate Meisenheimer Complex , 1996 .

[2]  E. Buncel,et al.  Ambident nucleophilic reactivity in .sigma.-complex formations. 6. Reactivity-selectivity relationships in reactions of ambident nucleophiles with the superelectrophiles 4,6-dinibrobenzofuroxan and 4,6-dinitro-2-(2,4,6-trinitrophenyl) benzotriazole 1-oxide , 1987 .

[3]  F. Terrier,et al.  Transient nitronic acid formation in the acid-catalyzed decomposition of nitrobenzofuroxan and nitrobenzofurazan .sigma.-adducts in methanolic solution. A kinetic study , 1985 .

[4]  J. Verchere,et al.  Kinetic study of the proton-transfer reactions involving kryptopyrrole and its cation in aqueous solution. Transition-state structure determinations , 1985 .

[5]  M. Brechbiel,et al.  Benzidine rearrangements. 18. Mechanism of the acid-catalyzed disproportionation of 4,4'-diiodohydrazobenzene. Application of heavy-atom kinetic isotope effects , 1983 .

[6]  C. F. Bernasconi,et al.  Intermediates in nucleophilic aromatic substitution. 20. Rate-limiting proton transfer in the formation of Meisenheimer complexes between 1,3,5-trinitrobenzene and amines. The effect of dimethyl sulfoxide on proton-transfer rates. Relative leaving-group abilities of amines and alkoxide ions , 1979 .

[7]  R. O'ferrall,et al.  Aromatic protonation. XII. Solvent isotope effects in H/sub 2/O--D/sub 2/O mixtures on the detritiation of trimethoxybenzene , 1977 .

[8]  E. Buncel,et al.  Equilibrium protonation of the 1,3,5-trinitrobenzene–phenoxide σ-complex , 1976 .

[9]  E. Murrill,et al.  Vinyl ether hydrolysis. III. Broensted relations and transition state structure , 1971 .