Fotokemijske reakcije stiril-derivata furana, pirola i tiofena

undergraduate thesis

• Title (english): Photochemical reaction of styryl-derivatives of furan, pyrrole and thiophene
• Author: Ivan Peretin
• Mentor: Dragana Vuk (mentor)
• Committee member: Dragana Vuk (predsjednik povjerenstva)
• Committee member: Ivana Šagud (član povjerenstva)
• Committee member: Marijana Kraljić Roković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-09-22, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Rad sadržava pregled fotokemijskih reakcija 2- i 3-supstituiranih furanskih derivata o-divinil benzena, stiril-supstituiranih kondenziranih derivata furana, disupstituiranih stiril-derivata furana te distirilfuranskih derivata. 2- supstituirani furanski derivati o-divinilbenzena kao glavni produkt daju intramolekulske [2+2] benzobicklo[3.2.1]okta-2,6-dienske fotocikloadukte, 3- supstituirani furanski derivati o-divinilbenzena [2+2] fotocikloadicijske benzobiciklo[2.1.1]heksenske strukture preko 1,4-biradikalskog intermedijera. Stirilbenzofuran daje biciklički cikloadukcijski glavni produkt, dok stirilnaftofuranski derivati formiraju većinski dimerne produkte. Disupstituirani stiril-derivati furana kao glavni produkti pri niskim koncentracija daju biciklo[3.2.1]oktadienski derivati, a pri visokim koncentracijama daju ciklofanske strukture nastale dvostrukom intermolekularnom syn glava-glava [2+2]-cikloadicijom. Osvjetljavanjem 2-tienil supstituiranog o-divinilbenzena kao glavni produkt izoliran je tieno-kondenzirani benzobiciklo[3.2.1]oktadien, a potvrđene su i manje količine fenantrena i vinilnaftotiofena. Osvjetljavanje 3-tienil supstituiranog o-divinilbenzena daje, ne samo očekivani biciklo[3.2.1]oktadienski derivat, već i biciklo[2.1.1]heksenski derivat. β, β'-disupstituirani 5-H/Me/Br-2-tienil-derivati daju dihidronaftalenske derivate kao glavni produkt. U slučaju nesupstituiranog 2-tienilnog derivata izoliran je i dimerni produkt. β, β'-disupstituiranih 3-tienil- i 3-benzotienil-derivati o-divinilbenzena daju fuzionirani triciklički spoja, ciklofanski produkt te dimerni fotoprodukt.

Abstract (english)

This work contains overview of photochemical reactions of 2- and 3-supstituted furan derivates of o-divynylbenzenes, styrl-substituted annelated furane derivates, disubstituted styryl- furan derivates. 2-substituted furan o-divynyl derivates give intramolecular [2+2] benzobycyclo[3.2.1]octa-2,6-dieneas main photocycloaducts, 3-substituted 3-furan o-divynyl derivates give [2+2] photocycloaducts via 1,4-biradical intermediate. Styrylbenzofurane gives bicyclo cycloaduct as main product, while styrylnaphtofurane derivates give mostly dimeric products. Disupstituted styryl furane derivates give bicyclo[3.2.1]octadiene products at low concentrations, and cyclophane products formed via intermolecular syn head-head [2+2]-cycloaddition at high concentrations . By irradiotion of 2-tienyl substituted o-divynylbenzene benzobicyclo[3.2.1]octadiene is isolated as main product. Irradiation of 3-tienyl supstituted o-divynylbenzene gives expected bicyclo[3.2.1]octadiene derivate with bicyclo[2.1.]hexene derivate. β, β'-disupstituted 5-H/Me/Br-2-tienyl-derivates give dihydronaphtalene derivates as main product. In case of unsupstituted 2-tienyl derivate dimeric product is also isolated. β, β'-disupstituted 3-tienyl- i 3-benzotienyl o-divynylbenzene derivates give fused tricyclic compound, cyclophane and dimeric products.

• Keywords: furan; tiofen; benzobiciklo[3.2.1]oktadien; cikloadicija; dimerni produkt
• Keywords (english): furan; thiophene; benzobicyclo[3.2.1]octadiene; cycloaddition; dimeric product
• Language: croatian
• URN:NBN: urn:nbn:hr:149:677755
• Study programme: Title: Materials Science and Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-06-10 12:26:39