Fotokatalitske pretvorbe nekaterih 3-(alkilamino)propenoatov

diplomsko delo

Tilen Zorko (Author), Bogdan Štefane (Mentor)

Abstract

Enaminoni so spojine, za katere sta značilni karbonilna in aminska substituenta ob dvojni vezi. So pomembni gradniki v organski sintezi, predvsem pri pripravi heterocikličnih spojin. V diplomskem delu sem se osredotočil na fotokemijsko oksidacijo dušika na različnih enaminonih in ujetje nastalega radikala z elektronsko revnimi alkeni. Velik del diplome sem posvetil izbiri ustreznega fotoredoks katalizatorja. Najbolj logična izbira iz vidika zelene kemije je bila uporaba nekovinskih katalizatorjev, ki nudijo dovolj visoke potenciale za uspešno oksidacijo enaminonov. Najprej sem reakcijo izvajal z akridinijevim katalizatorjem, pri katerem je nastanek črne barve oviral potek reakcije in znižal izkoristek pretvorbe. Da bi preprečili nastanek črne barve in izboljšali reaktivnost sistema, sem raziskal vpliv katalizatorjev in alkenov, na potek reakcije. Antrakinonski katalizator je zvišal izkoristke pretvorb in ohranil prosojnost raztopine, zato sem lahko nadalje izvedel optimizacijo in razširil reakcijsko metodo na različne vrste enaminonov. Reakcija poteka zgolj v kloriranih topilih, zato sem končne produkte sintetiziral v 1,2-dikloroetanu.

Keywords

enaminoni;fotokataliza;fotoredoks katalizatorji;svetloba;radikali;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2021
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[T. Zorko]
UDC:	547:544.526.5(043.2)
COBISS:	70493187
Views:	410
Downloads:	97
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Photocatalytic conversions of some 3-(alkylamino)propenoate
Secondary abstract:	Enaminones are compounds consisting of an amino group linked through a double bond to a carbonyl group. They are some of the most frequently employed building blocks in organic, especially heterocyclic synthesis. In my undergraduate thesis, I focused on photochemical oxidation of nitrogen in enaminones. Special attention was given to the selection of appropriate photoredox catalyst. The most logical choice were organic photoredox catalysts, which offer metal-free alternatives to transition metal catalyzed reactions, while also providing appropriate reduction potentials. First attempts of enaminone conversion were done with acridinium photocatalyst. An instant change in color from transparent yellow to dark brown was observed within few minutes, which dramatically decreased reaction yield. Hence, I was trying to prepare an alternative method, which would preserve transparency of solution throughout the duration of the reaction. The best results were obtained while using anthraquinone as catalyst. Optimized reaction method was than tested on different types of enaminones. Best yields were obtained, when 1,2-dichloroethane was employed as a solvent.
Secondary keywords:	enaminones;photoredox catalysis;light;radical;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	33 str.
ID:	13085132