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Sinteza 1,3,4,5-štirisubstituiranih 1,2,3-triazolijevih soli
ID Rakar, Anastazija (Author), ID Košmrlj, Janez (Mentor) More about this mentor... This link opens in a new window

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Abstract
Sintetizirali smo dve 1,3,4,5-štirisubstituirane 1,2,3-triazolijeve soli, 3,4-difenil-5-metil-1-(p-tolil)-1H-1,2,3-triazolijev triflat in 3,4-difenil-5-etil-1-(p-tolil)-1H-1,2,3-triazolijev triflat. Sintezo smo začeli s 4-aminotoluenom, ki smo ga pretvorili v 4-azidotoluen. Med njim in fenilacetilenom smo izvedli z bakrom katalizirano azid-alkin cikloadicijo in dobili 1,4-disubstituiran-1,2,3-triazol. Tega smo reagirali z jodonijevo soljo v prisotnosti bakrovega sulfata in dobili 1,3,4-trisubstituirano 1,2,3-triazolijevo sol. V zadnji stopnji smo na mesto 5, v prisotnosti reagentov n-butillitija in ustreznega alkil jodida (metil jodida oziroma etil jodida), vezali metilno ali etilno skupino ter dobili produkta.

Language:Slovenian
Keywords:Sinteza, triazoli, »klik kemija«, triazolijeve soli
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2024
PID:20.500.12556/RUL-161322 This link opens in a new window
COBISS.SI-ID:214230531 This link opens in a new window
Publication date in RUL:10.09.2024
Views:153
Downloads:447
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Secondary language

Language:English
Title:Synthesis of 1,3,4,5-Tetrasubstituted 1,2,3-Triazolium Salts
Abstract:
We synthesized two 1,3,4,5-tetrasubstituted 1,2,3-triazolium salts, 3,4-diphenyl-5-methyl-1-(p-tolyl)-1H-1,2,3-triazolium triflate and 3,4-diphenyl-5-ethyl-1-(p-tolyl)-1H-1,2,3-triazolium triflate. The synthesis began with 4-aminotoluene, which was converted into 4-azidotoluene. A copper-catalyzed azide-alkyne cycloaddition was performed between it and phenylacetylene, resulting in 1,4-disubstituted-1,2,3-triazole. This compound was reacted with an iodonium salt in the presence of copper sulfate, resulting in a 1,3,4-trisubstituted 1,2,3-triazolium salt. In the final step, a methyl or ethyl group was attached at position 5 using n-butyl-lithium and corresponding alkyl iodide (methyl iodide or ethyl iodide), producing the respective products.

Keywords:Synthesis, triazoles, »click chemistry«, triazolium salts

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