Ločevanje regioizomerov fluoriranih organskih molekul z ustreznimi kemijskimi metodami

Lavrič, Jure (avtor), Gazvoda, Martin (mentor)

V modernem svetu si življenja brez fluoriranih spojin ne moramo predstavljati. Fluorirane spojine uporabljamo v farmaciji, poljedelstvu, prav tako se uporabljajo kot topila in korozijsko odporne plastične mase. Iz opisanega sledi, da je vez C–F ena izmed pomembnejših v organski kemiji. V sklopu diplomskega dela smo uspešno fluorirali štiri substrate. Produkti so bili sintetizirani s paladijem kataliziranim elektrofilnim aromatskim fluoriranjem, pri čemer smo uporabili Selectfluor kot vir fluora, paladijev kompleks kot katalizator in fenantrolin kot ligand. Spreminjali smo reakcijske pogoje, kot sta temperatura (50 °C in 80 °C) in reakcijski čas (24 in 72 ur) ter spremljali njihov vpliv na pretvorbo izhodnih substratov v produkte. Pretvorbo smo določili s pomočjo internega standarda 4-fluorobenzotrifluorid in 19F NMR spektroskopije. Pri reakcijah sta običajno nastala dva fluorirana regioizomerna produkta, za ločevanje katerih smo uporabili več različnih metod, kot sta kolonska kromatografija in destilacija.

• Jezik: Slovenski jezik
• Ključne besede: Selectfluor, elektrofilno aromatsko fluoriranje, paladijev katalizator, regioselektivno fluoriranje
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2021
• PID: 20.500.12556/RUL-127668
• COBISS.SI-ID: 69555203
• Datum objave v RUL: 18.06.2021

LAVRIČ, Jure, 2021, Ločevanje regioizomerov fluoriranih organskih molekul z ustreznimi kemijskimi metodami [na spletu]. Diplomsko delo. [Dostopano 18 maj 2025]. Pridobljeno s: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=slv&id=127668

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Methods for separation of regioisomers of fluorinated organic molecules

Izvleček

It is hard to imagine the modern world without fluorinated organic compounds. Fluorinated organic compounds are used as pharmaceuticals, agrochemicals and are also employed as solvents and corrosion resistant plastics. Considering all the above we can conclude that the C–F bond is one of the most imporant bonds in organic chemistry. In this diploma thesis, we fluorinated four substrates by palladium catalyzed electrophilic aromatic fluorination in which Selectfluor was used as a source of fluorine, palladium complex as the catalyst and phenantroline as the ligand. We altered the reaction conditions such as temperature (50 °C and 80 °C) and reaction time (24 and 72 hours) and monitored their effect on the conversion of starting materials into products. The conversions into products were determined by 19F NMR using 4-fluorobenzotrifluoride as the internal standard. For the separation of the regioisomers of fluorinated products we used different methods such as column cromatography and destilation.

• Ključne besede: Selectfluor, electrophilic aromatic fluorination, palladium catalyst, regioselective fluorination