20.500.12556/RUL-127984 Sinteza izbranih aromatskih in heteroaromatskih geminalnih dibromoalkenov The Synthesis of Selected Aromatic and Heteroaromatic Geminal Dibromoalkenes V sklopu diplomskega dela smo pretvorili različne aldehide v pripadajoče geminalne dibromoalkene z modificiranim postopkom prve stopnje Corey-Fuchsove reakcije, znane tudi pod imenom Ramirezova olefinacija. Ledeno hladnim raztopinam komercialno dostopnih aldehidov v diklorometanu smo dodali tetrabromometan in trifenilfosfin, ki in situ tvorita ilid, ta pa reagira z izhodnim aldehidom do pripadajočega gem-dibromoalkena. Uspešno smo sintetizirali sedem (het)aromatskih 1,1-dibromoalkenov iz komercialno dostopnih aldehidov, izmed katerih sta bila dva monohalogenirana, dva sterično ovirana, po en z elektron-donorsko in elektron-privlačno skupino, zadnji izmed njih pa je bil heteroaromatski. Produkte smo izolirali, očistili s kolonsko kromatografijo na SiO2, okarakterizirali z 1H NMR in IR spektroskopijo ter preverili njihovo čistost s HPLC kromatografijo. Trdnim produktom smo določili tudi tališča. Uspešnost pretvorb smo primerjali med sabo in ugotovili, da večina njih poteče z visokimi in primerljivimi izkoristki. As a part of my Bachelor's thesis a series of aldehydes were converted into corresponding geminal dibromoalkenes via first step of the Corey-Fuchs reaction, also known as Ramirez olefination. Ice cold aldehyde solutions in dichloromethane were treated with the ylide, which was formed in situ from tetrabromomethane and triphenylphosphine. Subsequently, the aldehydes were converted into corresponding gem-dibromoalkenes. We have successfully synthesised seven (het)aromatic 1,1-dibromoalkenes from the starting aldehydes, two of which were monohalogenated benzaldehydes, two were sterically hindered, one contained an electron-accepting and the other electron-donating functional group, and one was a heteroaromatic aldehyde. The products were isolated, purified by silica gel column chromatography and characterized by 1H NMR and IR spectroscopy. The purity of the synthesized products was determined by HPLC chromatography and the melting points of the solid products were also determined. Comparison of the conversions of different substrates revealed that most of the aldehydes were readily converted into the desired products. geminalni dibromoalken Corey-Fuchsova reakcija aldehid trifenilfosfin geminal dibromoalkene Corey-Fuchs reaction aldehyde triphenylphosphine true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2021-06-30 15:40:00 2021-06-30 15:40:01 2022-09-07 04:12:33 0000-00-00 00:00:00 2021 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 14081 70759427 Hofferle_Jakob_-_Sinteza_izbranih_aromatskih_in_heteroaromatskih_geminalnih_dibromoalkenov.pdf Hofferle_Jakob_-_Sinteza_izbranih_aromatskih_in_heteroaromatskih_geminalnih_dibromoalkenov.pdf 1 12BE0B9D75D21495A9C34CBFCAD3AFAD 05ff8e78f30244cd3864b68f51ab1e1e703bc8994a107538e06673ac46c2fc18 8c0ed027-d9a8-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=144608 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0