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Pri diplomskem delu smo se ukvarjali s sintezo izbranih geminalnih dibromoalkenov. Le-te smo pripravili iz vrste komercialno dostopnih aromatskih in heteroaromatskih aldehidov. Sintezo smo izvedli preko prve stopnje Corey-Fuchs sinteze, kjer smo izhodnemu aldehidu dodali trifenilfosfin in tetrabromometan. Med slednjima se je tvoril pripadajoči ilid, ki je reagiral z izhodnim aldehidom pri čemer se je tvoril želeni geminalni dibromoalken. Uspešno smo sintetizirali pet aromatskih in dva heteroaromatska geminalna dibromoalkena. Pripravljene produkte smo izolirali in očistili s kolonsko kromatografijo na SiO2, okarakterizirali z 1H NMR in IR spektroskopijo ter jim določili čistost s HPLC kromatografijo. Trdnim produktom smo prav tako določili tališča. During my Bachelor’s thesis the synthesis of series of geminal dibromoalkenes was successfully achieved. Herein presented geminal dibromoalkenes were synthesized starting from commercially available aromatic and heteroaromatic aldehydes. The synthesis was done through the first step of Corey-Fuchs reaction, where triphenylphosphine and tetrabromomethane were added to the starting aldehyde. Triphenylphosphine and tetrabromomethane in situ formed ylide, which then reacted with desired aldehyde, resulting in geminal dibromoalkene formation. Five aromatic and two heteroaromatic geminal dibromoalkenes were successfully synthesized. Herein prepared products were isolated, purified by column chromatography on SiO2 and characterized by 1H NMR and IR spectroscopy. The purity of synthesized products was determined using HPLC chromatography. The melting points of solid products were also measured. |
