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master's thesis
Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:898437
Lukač, Matej
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Lukač, M. (2018). Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:898437

Lukač, Matej. "Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:898437

Lukač, Matej. "Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:898437

Lukač, M. (2018). 'Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 17 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:898437

Lukač M. Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2024 November 17] Available at: https://urn.nsk.hr/urn:nbn:hr:149:898437

M. Lukač, "Funkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:898437

Metadata
TitleFunkcionalizacija heterocikličkih benzobiciklo[3.2.1]oktadienskih sustava
Title (english)Functionalization of heterocyclic benzobicyclo[3.2.1]octadiene systems
AuthorMatej Lukač
MentorDragana Vuk (mentor)
Committee memberDragana Vuk (predsjednik povjerenstva)
Committee memberIrena Škorić (član povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-11-30, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Fotokatalitičke oksigenacije predstavljaju tip homogene fotokatalitičke reakcije pomoću kojih se molekularni kisik na vrlo jednostavan način uz pomoć svjetlosti ugrađuje u produkte. U ovome radu ispitan je utjecaj naboja Mn(III) porfirina, koncentracije kisika te položaja heteroatoma u prstenu na tijek i mehanizam reakcija fotokatalitičke oksigenacije na tiofenskim derivatima koji sadrže biciklo[3.2.1]oktadiensku strukturu, koja je kostur brojnih važnih biološki aktivnih prirodnih spojeva i njihovih metabolita. Reakcije fotokatalitičke oksigenacije provedene su osvjetljavanjem u smjesi aceton-voda (50:50) uz anionski ili kationski manganov(III) porfirin kao katalizator, čime se izbjegla upotreba toksičnih otapala, te propuhivanjem kisikom ili zrakom pri pH 10. Početni prekursori 1 i 2 dobiveni su Wittigovom reakcijom iz difosfonijeve soli i odgovarajućeg aldehida, nakon čega su podvrgnuti fotokemijskoj reakciji. Fotokemijskom reakcijom sintetizirani su biciklički tiofenski sustavi 3 i 4, s različitim položajem heteroatoma u prstenu. Spojevi 3 i 4 podvrgnuti su zatim reakciji fotokatalitičke oksigenacije čime je dobiven niz oksigeniranih fotoprodukata: hidroksida, hidroperoksida i ketona, koji su u potpunosti spektroskopski okarakterizirani.
Abstract (english)
Photocatalytic oxygenation reactions are a type of homogeneous photocatalytic reactions in which molecular oxygen is incorporated into products. In this work, impact of Mn(III) porphyrin catalyst, oxygen concentration and position of heteroatom on the course and mechanism of the photocatalytic oxygenation reactions was investigated. Reactions were performed on the thiophene derivatives containing the bicyclo[3.2.1]octadiene moiety, which is the skeleton of many important biologically active natural compounds and their metabolites. Photocatalytic oxygenations were conducted in the presence of anionic or cationic manganese porphyrin as a catalyst, at pH 10 in oxygen- or air-saturated system. Initial precursors 1 and 2 were obtained by Wittig reaction from diphosphonic salt and the corresponding aldehyde, followed by photochemical reaction. Irradiation of starting compounds 1 and 2 gave bicyclic thiophene systems 3 and 4. Compounds 3 and 4 are then subjected to photocatalytic oxygenation reaction, resulting with a series of oxygenated photoproducts: hydroxides, hydroperoxides and ketones, which were completely spectroscopic characterized.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:898437
Study programmeTitle: Chemical Engineering - Graduate study
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra inženjer/inženjerka kemijskog inženjerstva (magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
Type of resourceText
File originBorn digital
Access conditionsOpen access
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Created on2022-02-23 12:22:56