Publications Scientifiques

[ Article ] Electronic and steric effects in the control of the Anilinium chloride catalyzed condensation reaction between Aldones and 4-Phenylthiosemicarbazide

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],
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)

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