20.500.12556/RUL-117332 Sinteza biciklo[2.2.2]oktenov iz različnih 2H-piran-2-onov ter maleimida oziroma njegovih derivatov kot osnova za raziskovanje halogenskih vezi Synthesis of bicyclo[2.2.2]octenes from various 2H-pyran-2-ones and maleimide or its derivatives as a basis for investigating halogen bonding V prvi fazi magistrskega dela sem sintetiziral serijo biciklo[2.2.2]oktenov iz primerno substituiranih 2H-piran-2-onov ter maleimida. Reakcije so potekale v skladu s pričakovanji dobro poznanih Diels–Alderjevih cikloadicij. Pripravljeni biciklo[2.2.2]okteni so predstavljali izhodne spojine v naslednji stopnji, t.j. reakciji N-halogeniranja, kjer sem želel ustvariti vez med halogenom (klorom) ter obročnim dušikovim atomom. Z modifikacijo postopkov iz literature sem tako razvil okolju prijazno N-kloriranje. Uporabil sem NaCl, ki je bil vir klora, oksidant okson, trdni Al2O3 ter kloroform kot topilo. Reakcije sem izvajal v zaprti ACE cevki pri temperaturi 45 °C, s spreminjanjem reakcijskih pogojev sem na ta način uspešno pripravil tri nove N,N'-dikloro derivate pripojenih biciklo[2.2.2]oktenskih sistemov. V drugi fazi eksperimentalnega dela sem poizkusil iz predhodno sintetiziranih N-halogeniranih biciklo[2.2.2]oktenov in ustreznih piridinskih derivatov pripraviti kokristale, ki bi vsebovali halogensko vez. Za ta namen sem kot akceptorja halogenske vezi uporabil 2,2'-bipiridil ter 4,4'-bipiridil, kar bi omogočilo nadaljnje raziskave narave halogenske vezi. Žal priprava kristalov ni uspela. In the first phase of my master's thesis, I synthesized a variety of bicyclo[2.2.2]octenes from suitably substituted 2H-pyran-2-ones and maleimide. The reactions were took place according to the well known Diels–Alder cycloadditions. The prepared bicyclo[2.2.2]octenes represented the starting reactant in the following step of N-halogenation reaction where I tried to form a bond between a halogen (chlorine) and a ring nitrogen. By appropriate modifications of the literature reaction conditions, I developed environmentally friendly N-chlorination, using NaCl, which was the source of chlorine, oxone as the oxidant, solid Al2O3, and chloroform as the solvent. The reactions were carried out in closed ACE tubes at 45 °C. By changing the reaction parameters I managed to successfully synthesize three new N,N'-dichloro derivatives of fused bicyclo[2.2.2]octene systems. In the second phase of the experimental work, I tried to prepare co-crystals from previously synthesized N-halogenated bicyclo[2.2.2]octenes and suitable pyridine derivatives, which would presumably contain halogen bond, using 2,2'-bipyridyl and 4,4'-bipyridyl, as the halogen bond acceptors. Preparation of such crystals would allow further investigations into the nature of halogen bonding. Unfortunately, the preparation of the crystals was not successful. 2H-piran-2-oni Diels–Alderjeva reakcija biciklo[2.2.2]okteni halogenirani biciklo[2.2.2]okteni halogenska vez. 2H-pyran-2-ones Diels–Alder reaction bicyclo[2.2.2]octenes halogenated bicyclo[2.2.2]octenes halogen bond. true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2020-07-07 14:45:01 2020-07-07 14:45:10 2022-08-29 03:42:42 0000-00-00 00:00:00 2020 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 6227 22864131 Kos_Grega_-_Sinteza_biciklo[2.2.2]oktenov_iz_razlicnih_2H-piran-2-onov_ter_maleimida_oziroma_nje.pdf Kos_Grega_-_Sinteza_biciklo[2.2.2]oktenov_iz_razlicnih_2H-piran-2-onov_ter_maleimida_oziroma_nje.pdf 1 33F2460BA15D5B958EC3ED1B2CF49E1D 33d679b48ba8b1e0393ad13e2298bab5017f410627f39481b56c3ce1d07c2ba9 27a6f381-a1b9-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=131161 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0