20.500.12556/RUL-129254 Sinteza različno substituiranih biciklo[2.2.2]oktenskih sistemov z uporabo maleinanhidrida in njegovih derivatov Synthesis of various substituted bicyclo[2.2.2]octene systems with the use of maleic anhydride and its derivatives V okviru magistrske naloge sem sintetiziral osem različno substituiranih biciklo[2.2.2]oktenskih sistemov z dvojno termično Diels–Alderjevo cikloadicijo maleinanhidrida na različno substituirane 2H-piran-2-one. V prvi stopnji s cikloadicijo maleinanhidrida v vlogi dienofila nastanejo oksabiciklo[2.2.2]oktenski intermediati, ki pod reakcijskimi pogoji spontano eliminirajo molekulo ogljikovega dioksida in tako tvorijo naslednji cikloheksadienski intermediat, ki služi kot nov dien za napad nove molekule dienofila (maleinanhidrida). Z molekulskim modeliranjem sem raziskal ali je v prvi stopnji cikloadicij različnih dienofilov (maleinanhidrida in substituiranih vinil etrov) reakcijski napad preferenčno ekso ali endo. Rezultate, dobljene z računsko metodo PM6, sem primerjal z eksperimentalnimi podatki, vključno z že objavljenimi v literaturi. In this master's degree I have synthesized eight variously substituted bicyclo[2.2.2]octene systems by using Diels–Alder cycloaddition of maleic anhydride on differently substituted 2H-pyran-2-ones. In the first stage of the cycloaddition of maleic anhydride as the dienophile oxabicyclo[2.2.2]octene intermediates are formed, which under the reaction conditions spontaneously eliminate a molecule of carbon dioxide and thus form the next cyclohexadiene intermediate, which serves as the diene for the attack of the second molecule of dienophile (maleic anhydride). Using molecular modelling I explored the endo/exo attack preference of various dienophiles (maleic anhydride and substituted vinyl ethers) of the first stage of the cycloaddition reaction. I compared the results, obtained with the computational method PM6, with experimental data in the literature. Diels–Alderjeva reakcija biciklo[2.2.2]oktenski sistemi maleinanhidrid 2H-piran-2-oni molekulsko modeliranje Diels–Alder reaction bicyclo[2.2.2]octene maleic anhydride 2H-pyran-2-one molecular modelling true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2021-08-31 14:25:00 2021-08-31 14:25:06 2022-09-08 04:07:32 0000-00-00 00:00:00 2021 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 9441 76775171 Sinkovec_Aljaz_-_Sinteza_razlicno_substituiranih_biciklo[2.2.2]oktenskih_sistemov_z_uporabo_male.pdf Sinkovec_Aljaz_-_Sinteza_razlicno_substituiranih_biciklo[2.2.2]oktenskih_sistemov_z_uporabo_male.pdf 1 05281ADFCFCB8E2668335D5B4AB7DEB2 a3b2b3ba8783fd5ad4484a9c8cc58a3aa30a01071bf2e155a04120a67791e403 3ee27410-0a56-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=146224 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0