Aromatic nucleophilic substitution. 20. Kinetics of the reactions of 2-(acetylamino) ethyl 2, 6-dinitrophenyl ether and N-acetyl-N-(2-hydroxyethyl)-2, 6-dinitroaniline with …

S Sekiguchi, M Hirai, N Tomoto

Index: Sekiguchi, Shizen; Hirai, Motohiko; Tomoto, Noboru Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2378 - 2381

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Abstract

Results Stage I. Rearrangement of 2-(Acety1amino) ethyl 2, 6-Dinitrophenyl Ether (le). As the spectral evidence shows, ll the reaction of le or 6e is divided into two stages. With le, ll the process le rr 2e e 3e (stage I) is very fast, whereas the process 3e rr 4e-5e (stage 11) is relatively slow. With 6e the process 6e rr 46 e 3e (stage I) is very fast, whereas the process 3e rr 4e-5 (stage 11) is relatively slow. Thus the stage I equilibrium is established rapidly, ...