Nucleophile Substitutionen an Kohlensäurederivaten. XII. Kinetik und Mechanismus der Reaktion von N‐Nitro‐N‐alkylurethanen mit primären aliphatischen Aminen
作者:
R. Bacaloglu,
Y. Prodan‐Deac,
C. Csunderlik,
P. Csomos,
期刊:
Journal für Praktische Chemie
(WILEY Available online 1980)
卷期:
Volume 322,
issue 1
页码: 10-20
ISSN:0021-8383
年代: 1980
DOI:10.1002/prac.19803220103
出版商: WILEY‐VCH Verlag GmbH
数据来源: WILEY
摘要:
Nucleophilic Substitutions to Carbonic Acid Derivates. XII. Kinetics and Mechanism of the Reaction of N‐Nitro‐N‐alkyl‐urethanes with Primary Aliphatic AminesThe aminolysis of N‐alkyl‐N‐nitrourethanes takes place, as the kinetical studies demonstrate, by means of several consecutive steps.The nucleophilic attack of the amine (first step; reaction B), as well as the proton‐transfere (second step; reaction C), are quick pre‐equilibres, followed by the slow, rate‐determining elimination of the nitramino‐group (reaction D).During the deprotonation, an intermediate with two to the nitramino‐group antiperiplanar orbitals is formed, providing the necessary mesomeric assist
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