TITLE

O-nucleophilic features of amidoximes in acyl group transfer reactions

AUTHOR(S)
Prokop'eva, T. M.; Simanenko, Yu. S.; Karpichev, E. A.; Savelova, V. A.; Popov, A. F.
PUB. DATE
November 2004
SOURCE
Russian Journal of Organic Chemistry;Nov2004, Vol. 40 Issue 11, p1617
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Analysis of kinetic behavior of isomericZ-amidoximes and theirZ-ions in reactions with 4-nitrophenyl-4-toluenesulfonate, diethylphosphate, and diethylphosphonate was performed in the framework of Bronsted relationship. The reactivity of amidoximate anions with respect to the mentioned substrates is comparable to that of typical a-nucleophiles, oximate ions. The a-effect decreased with the growing basicity of amidoximate ions, and for compounds with pKa>12.0 it was totally lacking. The high nucleophilic activity of neutral amidoximes and their anionic forms was ascribed to the cyclic structure of the transition state involving two kinds of assistance: general acidic, and basic catalysis. A unique feature of amidoximes as a-nucleophiles consists in their ability to perform efficient cleavage of ecotoxic substrates in a wide pH range, from basic to acid media.
ACCESSION #
16904090

 

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