20.500.12556/RUL-109654 Razvoj metode za gem-dimerizacijo terminalnih acetilenov Development of synthetic procedure for gem-dimerization of terminal alkynes V magistrskem delu smo se ukvarjali z razvojem metode za selektivno gem-dimerizacijo terminalnih acetilenov. Na primeru modelne reakcije fenilacetilena (1a) smo optimizirali reakcijske pogoje, to je izbira katalizatorja, topila, temperature in reakcijskega časa. Kot izhodne substrate smo uporabili različne aromatske in alifatske acetilene. V literaturi je mogoče zaslediti podatke o temperaturni občutljivosti eninov, zato smo analizirali stabilnost izbranih produktov. Razvili smo metodo za izolacijo in čiščenje nastalih produktov, ki smo jih karakterizirali z NMR tehnikami. S tako pripravljenimi gem-enini smo preverili njihovo uporabnost za Heckovo reakcijo. Z uporabo stabilnega enina 2f* in 4-jodotoluena (4a) smo v prisotnosti PEPPSI Pd-tzNHC kompleksa uspeli pripravili želen trisubstituiran produkt. This work is aimed to describe the development of a method for the selective gem-dimerization of terminal acetylenes. In the case of the model reaction of phenylacetylene (1a), the reaction conditions were optimized through the choice of catalyst, solvent, temperature and reaction time. Various aromatic and aliphatic acetylenes were used as starting substrates. Data on the temperature sensitivity of enynes can be traced in the literature, prompting us to analyze stability of the selected products. We have developed a method for isolating and purifying the resulting products, which were characterized by NMR techniques. With the gem-enynes prepared in this way, we tested their usefulness for the Heck reaction. Using the stable enyne 2f* and 4-iodotoluene (4a), we were able to prepare the desired trisubstituted product in the presence of a PEPPSI Pd-tzNHC complex. enin acetilen dimerizacija paladijevi kompleksi Heckova reakcija enyne acetylene dimerization palladium complex Heck reaction true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2019-09-06 10:50:13 2019-09-06 10:50:14 2022-08-21 03:43:35 0000-00-00 00:00:00 2019 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 6606 1538401475 Pavcnik_Tjasa_-_Razvoj_metode_za_gem-dimerizacijo_terminalnih_acetilenov.pdf Pavcnik_Tjasa_-_Razvoj_metode_za_gem-dimerizacijo_terminalnih_acetilenov.pdf 1 B02A7A6314EDEBFFAFAA014D1DC38AC7 f468a245765eaecc091f73e6c7ace83aac5db8dce07c4d207c179966a328078b ebd40b22-a1b6-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=121239 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0