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Razvoj metode za gem-dimerizacijo terminalnih acetilenov
Pavčnik, Tjaša (Author), Košmrlj, Janez (Mentor) More about this mentor... This link opens in a new window

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Abstract
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.

Language:Slovenian
Keywords:enin, acetilen, dimerizacija, paladijevi kompleksi, Heckova reakcija
Work type:Master's thesis/paper (mb22)
Tipology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2019
COBISS.SI-ID:1538401475 This link opens in a new window
Views:613
Downloads:199
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Secondary language

Language:English
Title:Development of synthetic procedure for gem-dimerization of terminal alkynes
Abstract:
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.

Keywords:enyne, acetylene, dimerization, palladium complex, Heck reaction

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