Volume 55, Issue 10 pp. 2284-2290
Article

Reactions of N-alkenyl Thioureas with p-alkoxyphenyltellurium Trichlorides

Mykola Kut

Mykola Kut

Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod, 88000 Ukraine

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Maksym Fizer

Maksym Fizer

Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod, 88000 Ukraine

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Mikhajlo Onysko

Corresponding Author

Mikhajlo Onysko

Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod, 88000 Ukraine

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Vasil Lendel

Vasil Lendel

Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod, 88000 Ukraine

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First published: 15 August 2018
Citations: 12

Abstract

N-Аlkenyl thioureas, under the action of aryltellurium trichlorides, form the addition products N-{2-chloro-3-[dichloro(4-alkoxyphenyl)-tellanyl]propyl} thioureas or the intramolecular cyclization products 5-{dichloro(4-alkoxyphenyl)-telluromethyl}-2-phenylamino-4,5-dihydro-1,3-thiazole hydrochlorides. The reaction route depends on the nature of the substituent in the thiourea. The Fukui function reactivity indexes identify the electrophilic/nucleophilic centers and explain the possible cyclization reaction in the case of phenyl substituted thioureas. In the case of other substituents, the calculated values of partial atomic charges clearly predict that the addition reaction is more possible.

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