20.500.12556/RUL-149558 Sinteza prekurzorjev N-heterocikličnih karbenov na osnovi kafre Synthesis of camphor-based N-heterocyclic carbene precursors Dolga leta so karbeni veljali le za nestabilne reakcijske intermediate v organskih reakcijah. Vendar pa je sinteza stabilnih karbenov in njihov katalitski potencial v zadnjih letih pritegnila številne raziskovalce. V tem delu je naravno prisotna (1R)-(+)-kafra služila kot osnova za sintezo N-heterocikličnih karbenov (NHC-jev). Kafrino ogrodje, ki se pogosto uporablja za pripravo bifunkcionalnih organokatalizatorjev, je odlična osnova za sintezo želenih kiralnih molekul. Iz komercialno dostopne (1S)-(+)-kafrasulfonske kisline smo v sedmih korakih sintetizirali dva diastereomerna prekurzorja šestčlenskih NHC-jev, katerih katalitske sposobnosti smo preiskali. Z drugo, devetstopenjsko sintezo, ki je prav tako izhajala iz (1S)-(+)-kafrasulfonske kisline, smo v sledovih sintetizirali petčlenski NHC-prekurzor. For many years, carbenes were considered to be only unstable intermediates in organic reactions. However, the synthesis of stable carbenes and their catalytic potential has attracted many researchers in recent years. In this work, naturally occurring (1R)-(+)-camphor was used as a chiral backbone for the synthesis of N-heterocyclic carbenes (NHCs). The camphor framework, which is often used to prepare bifunctional organocatalysts, serves as an excellent base for the synthesis of chiral molecules of interest. Starting from the commercially available (1S)-(+)-10- camphor sulfonic acid, a seven-step synthesis was carried out, yielding two diastereomeric six-membered NHC precursors, whose catalytic abilities were investigated. Another nine-step synthesis was carried out, also starting from (1S)-(+)-10- camphorsulfonic acid, which gave a five-membered NHC precursor in trace amounts. N-heterociklični karbeni (NHC) organokataliza kafra N-heterocyclic carbene (NHC) organocatalysis camphor true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2023-09-07 11:28:24 2023-09-07 11:28:25 2023-09-19 14:17:11 0000-00-00 00:00:00 2023 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22131 165023491 Segina_Jan_-_Sinteza_prekurzorjev_N-heterociklicnih_karbenov_na_osnovi_kafre.pdf Segina_Jan_-_Sinteza_prekurzorjev_N-heterociklicnih_karbenov_na_osnovi_kafre.pdf 1 F1F25CCF23CA8624114B3BA27D4BE00E f8a1f7e26b774304cbd791b3d0c37e56715862dba77d7d6bc3f22d88caf57ffd e378b5ae-4d60-11ee-9934-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=174042 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0