Sinteza prekurzorjev N-heterocikličnih karbenov na osnovi kafre

magistrsko delo

Jan Šegina (Author), Uroš Grošelj (Mentor), Helena Prosen (Thesis defence commission member), Bogdan Štefane (Thesis defence commission member)

Abstract

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.

Keywords

N-heterociklični karbeni;NHC;organokataliza;magistrska dela;

Data

Language:	Slovenian
Year of publishing:	2023
Typology:	2.09 - Master's Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[J. Šegina]
UDC:	547.599.6(043.2)
COBISS:	165023491
Views:	24
Downloads:	6
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Synthesis of camphor-based N-heterocyclic carbene precursors
Secondary abstract:	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.
Secondary keywords:	N-heterocyclic carbene;organocatalysis;camphor;Kafra;Kataliza;Heterociklične spojine;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Type (COBISS):	Master's thesis/paper
Study programme:	1000375
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages:	78 str.
ID:	19908998