Titre |
Electronic and steric effects in the control of the Anilinium chloride catalyzed condensation reaction between Aldones and 4-Phenylthiosemicarbazide |
Auteurs |
Kasséhin Urbain C. [1],
Gbaguidi A. Fernand [2],
Kapanda Coco N. [3],
McCurdy Christopher R. [4],
Bigot André K. [5],
Poupaert Jacques H. [6],
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Journal: |
African Journal of Pure and Applied Chemistry |
Catégorie Journal: |
Internationale |
Impact factor: |
0 |
Volume Journal: |
7 |
DOI: |
10.5897/AJPAC2013. 0514 |
Resume |
A concise series of aldehydes and ketones were reacted in a condensation reaction with 4phenylthiosemicarbazide in order to assess the relative influence of the steric and electronic effects in the control of this reaction. While steric effects had a modest impact, electronic effects and in particular the mesomeric donating effect delivered by a phenyl ring produced a strong passivating influence on the reactivity of these aldones. Additionally, the cyclopropyl substituent totally passivated the reaction via the interfering factor of its inherent sigma-aromaticity. When reacted with cyclopropyl-phenylketone, under our standard conditions, 4-phenylthiosemicarbazide gave in 82%, an original 1, 4-dihydrotetrazine via a double consecutive self-condensation. |
Mots clés |
Thiosemicarbazone, electronic effect, steric effect, ion catalysis aniline, sigma, aromaticity |
Pages |
325 - 329 |
Fichier |
(PDF) |