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Ločevanje regioizomerov fluoriranih organskih molekul z ustreznimi kemijskimi metodami
ID Lavrič, Jure (Author), ID Gazvoda, Martin (Mentor) More about this mentor... This link opens in a new window

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Abstract
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.

Language:Slovenian
Keywords:Selectfluor, elektrofilno aromatsko fluoriranje, paladijev katalizator, regioselektivno fluoriranje
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2021
PID:20.500.12556/RUL-127668 This link opens in a new window
COBISS.SI-ID:69555203 This link opens in a new window
Publication date in RUL:18.06.2021
Views:1237
Downloads:224
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Secondary language

Language:English
Title:Methods for separation of regioisomers of fluorinated organic molecules
Abstract:
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.

Keywords:Selectfluor, electrophilic aromatic fluorination, palladium catalyst, regioselective fluorination

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