Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions

[img]PDF - Authorized users only
Language: English
165Kb
Title:Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions
Creators:
Macháček, Vladimír
Čegan, Alexandr
Halama, Aleš
Rožňavská, Olga
Štěrba, Vojeslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 60, 8, pp. 1367-1379

Abstract

<p>Azo coupling reactions of benzenediazonium salts with substituted 4-amino-3-penten-2-ones take place at the C-3 atom. <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy has been used to study the structure of both the starting enaminones and coupling products. In CDCl<sub>3</sub>, 3-(4-chlorophenylhydrazono)-2-(4-methylphenylimino)-4-pentanone exists in hydrazo form whereas 4-amino-3-(4-chlorophenylazo)-3-penten-2-one is present as a mixture of two azo compounds differing probably in the arrangement of the intramolecular hydrogen bond. The azo coupling reaction kinetics have been studied in acetate buffers and methanol-water or <i>tert</i>-butyl alcohol-water mixtures. The coupling rate has been found independent of pH and buffer concentration. The reaction orders with respect to the starting compounds have been determined and the reaction mechanism is suggested. Linear dependence has been found between log <i>k</i><sub>obs</sub> and substituent constants according to the Hammett or Yukawa-Tsuno equations.

Title:Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions
Creators:
Macháček, Vladimír
Čegan, Alexandr
Halama, Aleš
Rožňavská, Olga
Štěrba, Vojeslav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:60
Number:8
Page Range:pp. 1367-1379
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19951367UNSPECIFIED
ID Code:833
Item Type:Article
Deposited On:06 Feb 2009 17:04
Last Modified:06 Feb 2009 16:04

Citation

Macháček, Vladimír; Čegan, Alexandr; Halama, Aleš; Rožňavská, Olga; Štěrba, Vojeslav (1995) Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions. Collection of Czechoslovak Chemical Communications, 60 (8). pp. 1367-1379. ISSN 0010-0765

Repository Staff Only: item control page