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master's thesis
Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:109620
Horvat, Iva
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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Horvat, I. (2018). Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:109620

Horvat, Iva. "Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:109620

Horvat, Iva. "Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:109620

Horvat, I. (2018). 'Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:109620

Horvat I. Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:109620

I. Horvat, "Sinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:109620

Metadata
TitleSinteza novih biciklo[3.2.1]oktadienskih derivata fuzioniranih s tiofenskim prstenom
Title (english)Synthesis of new bicyclo[3.2.1]octadiene derivatives fused with thiophene ring
AuthorIva Horvat
MentorDragana Vuk (mentor)
Committee memberDragana Vuk (predsjednik povjerenstva)
Committee memberIrena Škorić (član povjerenstva)
Committee memberŠime Ukić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-07-12, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu provest će se funkcionalizacija biciklo[3.2.1]oktadienskog sustava fuzioniranog s tiofenskom jezgorm. Formiliranjem tiofenske jezgre dobiveni aldehid III podvrgnut je Wittigovoj reakciji da bi se dobili 2-tienilni sustavi 1 i 2 koji su zatim fotokemijski ciklizirani. Očekivano je dobivanje novih složenih policikličkih struktura ovisno o elektronskom utjecaju metilne i cijano skupine kao supstituenta. Fotokemijska reakcija metil-supstituiranog spoja 1 dovodi do nastanka ciklizacijskog produkta 3. Međutim, osvjetljavanjem spoja 2 ne dolazi do reakcije, te je izoliran samo početni spoj. Kako bi se ispitao utjecaj položaja heteroatoma na reakcijski mehanizam provela se i sinteza na 3-tienilnom sustavu. Provođenjem fotokemijske reakcije dobiven je biciklički derivat V koji reakcijom Vilsmeier-Haack-ovog formiliranja daje aldehid 4. Novosintetizirani spoj 4 podvrgnut je Wittigovoj reakciji u smislu priprave novih aneliranih sustava. Dobiveni produkt 5 izoliran je u 46 %-tnom iskorištenju te je podvrgnut fotokemijskoj ciklizaciji. Nakon 5 sati dobiven je ciklizacijski produkt 6 u iskorištenju od 28 %. Svi priređeni spojevi 1-6 okarakterizirani su modernim spektroskopskim metodama (1H NMR, 13C NMR, UV, IR).
Abstract (english)
In this work, functionalization of bicyclo[3.2.1]octadiene system fused with thiophene ring will be carried out. Aldehyde III obtained by Vilsmeier-Haack's formylation reaction of thiophene ring, underwent Wittig's reaction in terms of obtaining 2-thienyl systems 1 and 2, which were then photochemically cyclizated. Getting the new complex polycyclic structures depending on the electronic effects of methyl and cyano groups as substituents in the molecule was expected. Photochemical reaction of methyl-substituted compound 1 leads to the cyclization product 3. On the other hand, by illuminating the compound 2, no reaction was observed and only the starting compound was isolated. In order to examine the influence of the position of heteroatom on reaction mechanism, synthesis on 3-thienyl system was carried out. Bicyclic derivative V was obtained by photochemical reaction and then underwent formylation reaction. The new synthesized compound 4 underwent Wittig’s reaction in terms of obtaining new anelated systems. Obtained product 5 was isolated in 46 % yield and then underwent photochemical cyclization. After 5 h, cyclization product 6 was obtained with the yield of 28 %. All obtained compounds 1-6 were characterized by modern spectroscopic methods (1H NMR, 13C NMR, UV, IR).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:109620
Study programmeTitle: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2020-06-04 12:27:09