magistrsko delo
Martin Škrinjar (Author), Bogdan Štefane (Mentor), Jurij Lah (Thesis defence commission member), Franc Požgan (Thesis defence commission member)

Abstract

V sintezni organski kemiji je pomembna skupina reakcij vrste radikalske adicije s prenosom atoma (angl. Atom Transfer Radical Addition, ATRA), ki med drugim omogoča difunkcionalizacijo alkenov in alkinov z visoko atomsko ekonomičnostjo. Pri tovrstnih reakcijah gre za simultano vključevanje dveh funkcionalnih skupin v π-sistem. V literaturi lahko zasledimo, da so take reakcije uporabne za uvedbo skupin SCF$_3$ in SO$_2$CF$_3$ na različne alkene. Pri pregledu literature smo ugotovili, da obstaja dokaj neraziskano področje uvedbe funkcionalne skupine SCCl$_3$, ki bi jo lahko uvedli z uporabo cenovno dostopnega reagenta triklorometil tiohipoklorita. Bakrovi katalizatorji so se pri predhodnih raziskavah tovrstnih reakcij izkazali za zelo uporabne in hkrati tudi cenovno ugodne analoge Ir(III) in Ru(II) katalizatorjev. Z uporabo fotokatalizatorja [Cu(dmp)$_2$]BF$_4$ smo pri valovni dolžini 450 nm in uporabi ClSCCl$_3$ reagenta uspešno funkcionalizirali različne stirenske derivate in produkte izolirali z dobrimi izkoristki. Izkazalo se je, da je reakcija uporabna tudi na elektronsko deficitarnih alkenih akrilatnega tipa in alkinih fenil acetilenskega tipa, pri katerih smo ugotovili, da je prevladujoč produkt E-izomer.

Keywords

radikalske reakcije;radikalske adicije s prenosom atoma;ATRA;fotoreakcije;bakrovi fotokatalizatorji;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [M. Škrinjar]
UDC: 547.31:544.526.5(043.2)
COBISS: 242920963 Link will open in a new window
Views: 89
Downloads: 26
Average score: 0 (0 votes)
Metadata: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Other data

Secondary language: English
Secondary title: Visible light-induced functionalisation of alkenes and alkynes with trichloromethanesulfonyl chloride
Secondary abstract: In synthetic organic chemistry, an important group of reactions is the type of radical addition with atom transfer (Atom Transfer Radical Addition, ATRA), which enables the functionalization of alkenes and alkynes with high atomic efficiency. In these reactions, the simultaneous incorporation of two functional groups into the π-system occurs. The literature indicates that these reactions are useful for introducing SCF$_3$ and SO$_2$CF$_3$ groups into various alkenes. Upon reviewing the literature, we found that there is a relatively underexplored area of introducing the SCCl$_3$ functional group, which could be introduced using the cost-effective reagent trichloromethane sulfenyl chloride. Copper catalysts have proven to be highly effective and cost-effective analogues of Ru(III) and Ir(II) complexes in previous studies of such reactions. Using the photocatalyst [Cu(dmp)$_2$]BF$_4$ at a wavelength of 450 nm and ClSCCl$_3$ as the reagent, we have successfully functionalized various styrene derivatives and isolated them with good yields. The reaction also proved to be applicable to electron-deficient alkenes such as acrylate derivatives, as well as phenylacetylene-type alkynes, with E-isomer being the predominant product.
Secondary keywords: photocatalysis;radical addition;styrenes;ATRA;photoreactions;Fotokataliza;Stiren;Univerzitetna in visokošolska dela;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 1 spletni vir (1 datoteka PDF (61 str.))
ID: 26719455