S. Sekiguchi, M. Hirai, N. Tomoto
Sep 1, 1983
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Journal
Bulletin of the Chemical Society of Japan
Abstract
The kinetics of the reactions of 2-(acetylamino)ethyl 2,6-dinitrophenyl ether (Smiles rearrangement) and N-acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline with sodium isopropoxide in the DMSO–2-propanol mixture (20 : 80 v/v) was studied. Both reactions were found to rapidly produce the same spiro anionic σ complex, giving N-(2-acetoxyethyl)-2,6-dinitroaniline. Although the rates for formation of the complex were different in both reactions, the rates for rearrangement were the same.