Mono‐, Bis‐ und Trishydrazo‐ und ‐azoverbindungen der Tricyanbenzolreihe, II. Elektrochemische Untersuchungen der Titelverbindungen

The electroreduction of three series of benzoylacetaniiides has been investigated in benzonitrile at a platinum electrode. One series (I) contains substituents on the benzoyl moiety, the second (11) has the substituents on the anilide moiety, and the third (111) has substituents on both the anilide and benzoyl moieties. All of these compounds are reduced in a single irreversible two-electron process forming the corresponding dianion which abstracts protons from the media to saturate the anilide CO. A good linearity is obtained when the E,/Z value is plotted against the substituent constant of the substituents in the different series .

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Mono‐, Bis‐ und Trishydrazo‐ und ‐azoverbindungen der Tricyanbenzolreihe, I. Darstellung und Eigenschaften der Titelverbindungen

Rieser

Ismail

Abou‐Elenien

et al. 1981

Liebigs Ann. Chem.

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Die Halogenatome in 2-Brom-I ,3,5-benzoltricarbonitril (3) und Chlorbenzolpentacarbonitril (4) lassen sich glatt durch Phenylhydrazin substituieren. Auch in 2,4,6-Trichlor-1,3,5-benzoltricarbonitril(1) und 2,4,6-Trifluor-1,3,5-benzoltricarbonitril (2) konnen ein oder zwei Halogenatome leicht durch Phenylhydrazin substituiert werden, wobei die Monohydrazoverbindungen Sa, b sowie die Bishydrazoverbindungen 6a, b gebildet werden. Die Substitution aller drei Halogenatome durch Phenylhydrazin ist nur im Fall der Fluorverbindung 2 moglich und auch dann nur unter drastischen Bedingungen (Druck). In 6a kann das verbleibende Fluoratom auch durch Phenolat-Ionen, Alkyl-(Aryl-)thiolat-Ionen oder durch Amine nucleophil substituiert werden. Die Oxidation der Hydrazoderivate 5a -d, 6a -f und 7 mit Bleidioxid ergibt die entsprechenden Azoverbindungen 8 ad, 9 af und 10. Die chemischen und spektroskopischen Eigenschaften der Hydrazo-und Azoverbindungen werden beschrieben. Mono-, Bis-and Trishydrazo, and -azo Compounds in the Tricyanobenzene Series, I. -Synthesis and Properties of the Title CompoundsIn 2-bromo-l,3,5-benzenetricarbonitrile (3) and chlorobenzenepentacarbonitrile (4) the halogen atoms can easily be substituted for phenylhydrazine. Also in 2,4,6-trichloro-1,3,5-benzenetricarbonitrile (1) and 2,4,6-trifluoro-1,3,5-benzenetricarbonitrile (2) one or two halogen atoms can easily be replaced with phenylhydrazine forming the monohydrazo compounds 5a, b and the bishydrazo compounds 6a,b. The substitution of all three halogen atoms by phenylhydrazine is only possible under drastic conditions (pressure) using the fluorine compound 2. In 6a the remaining fluorine atom can also be replaced with phenolate ions, alkyl-(aryl-)thiolate ions or amines. Oxidation of the hydrazo derivatives 5 ad, 6a -f, and 7 with lead dioxide gives the azo compounds 8a -d, 9a -f , and 10. The chemical and spectroscopical properties of the hydrazo and azo compounds are described.In mehreren Arbeiten -6 ) wurde auf die nucleophile Substituierbarkeit von Halogenatomen in cyanaktivierten Aromaten wie z. B. 2,4,6-Trichlor-1,3 ,Y-benzoltricarbonitril (l), 2,4,6-Trifluor-1,3,5-benzoltricarbonitril (2), 2-Brom-l,3,5-benzoltricarbonitril (3) a) Jetzige Adresse:

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Mono‐, Bis‐ und Trishydrazo‐ und ‐azoverbindungen der Tricyanbenzolreihe, II. Elektrochemische Untersuchungen der Titelverbindungen

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ChemInform Abstract: MONO‐, BIS‐ AND TRISHYDRAZO‐, AND ‐AZO COMPOUNDS IN THE TRICYANOBENZENE SERIES. II. ELECTROCHEMICAL STUDIES OF THE TITLE COMPOUNDS

ChemInform Abstract: MONO‐, BIS‐ AND TRISHYDRAZO‐, AND ‐AZO COMPOUNDS IN THE TRICYANOBENZENE SERIES. II. ELECTROCHEMICAL STUDIES OF THE TITLE COMPOUNDS

Electroreduction of benzoylacetanilides in nonaqueous medium

Mono‐, Bis‐ und Trishydrazo‐ und ‐azoverbindungen der Tricyanbenzolreihe, I. Darstellung und Eigenschaften der Titelverbindungen

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