Sinteza z adamantanom substituirane triazolijeve soli

Rener, Ambrož (author), Košmrlj, Janez (mentor)

Cilj diplomske naloge je bil sinteza 1,3,4,5-tetrasubstituirane-1H-1,2,3-triazolijeve soli, ki vsebuje adamantan kot vsaj enega izmed substituentov. Za seznanitev s koraki sinteze smo najprej sintetizirali 1-(4-metilfenil)-3,4-difenil-5-metil-1H-1,2,3-triazol-3-ijev triflat. Po optimizaciji klik reakcije med 1-azidoadamantanom in fenilacetilenom smo na majhni skali smo uspešno sintetizirali 1-(adamantan-1-il)-3,4-difenil-1H-1,2,3-triazol-3-ijev triflat in 1-(adamantan-1-il)-3,4-difenil-5-metil-1H-1,2,3-triazol-3-ijev triflat. Te tri nove spojine smo okarakterizirali z jedrsko magnetno resonanco, infrardečo spektroskopijo in masno spektrometrijo ter jim določili tališča.

• Language: Slovenian
• Keywords: triazolijeva sol, adamantan, klik reakcija
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2025
• PID: 20.500.12556/RUL-171941
• COBISS.SI-ID: 253415427
• Publication date in RUL: 04.09.2025

Secondary language

• Language: English
• Title: Synthesis of an adamantane-substituted triazolium salt

Abstract

The aim of this Bachelor's thesis was synthesis of 1,3,4,5-tetrasubstituted-1H-1,2,3-triazolium salt containing adamantane moiety as at least one of the substituents. To familiarize with the synthesis process, we first synthesized 1-(4-methylphenyl)-3,4-diphenyl-5-methyl-1H-1,2,3-triazol-3-ium triflate. After optimizing the click reaction between 1-azidoadamantane and phenylacetylene, we successfully synthesized 1-(adamantan-1-yl)-3,4-diphenyl-1H-1,2,3-triazol-3-ium triflate and 1-(adamantan-1-yl)-3,4-diphenyl-5-methyl-1H-1,2,3-triazol-3-ium triflate on a small scale. We characterized these three novel compounds with nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry; their melting points were also determined.

• Keywords: triazolium salt, adamantane, click reaction