Sinteza i fotokemija β,β'-disupstituiranog 5-metil-2-furilnog derivata o-divinilbenzena

master's thesis

• Title (english): Synthesis and photochemistry of β,β'-disubstituted 5-methyl-2-furyl derivative of o-divinylbenzene
• Author: Željka Kuzmić
• Mentor: Dragana Vuk (mentor)
• Committee member: Dragana Vuk (predsjednik povjerenstva)
• Committee member: Irena Škorić (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-07-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U cilju proučavanja utjecaja heteroatoma i pH vrijednosti na tijek fotokemijske reakcije i formiranja novih policikličkih struktura, proučavan je difuranski derivat o-divinilbenzena 1. Spoj 1 sintetiziran je Wittigovom reakcijom te podvrgnut fotokemijskim reakcijama u kiselom i neutralnom mediju, pri čemu su sintetizirana četiri nova spoja. Kao glavni produkt fotokemijske reakcije u neutralnom mediju dobiven je biciklo[3.2.1]oktadienski derivat 3 intramolekulskom reakcijom cikloadicije. Fotokemijskom reakcijom u kiselom mediju dobiven je dihidronaftalenski derivat 5 kao posljedica protoniranja i 1,6-zatvaranja. Kao posljedica reakcije 10π elektrociklizacije dobiven je fenantrenski derivat 2, u neutralnom i kiselom mediju, koji pri sniženoj pH vrijednosti podliježe sekundarnoj 6π elektrociklizaciji te nastaje pirenski spoj 4. Svi produkti su izolirani i u potpunosti okarakterizirani.

Abstract (english)

In order to study the influence of heteroatom and pH values on photochemical reactions, difurane derivative of o-divinylbenzene 1 was studied. Compound 1 was synthesized by Wittig reaction and irradiated in neutral and acidic medium. Four new compounds were obtained. Bicyclo[3.2.1]octadiene derivative 3 was obtained as main product in neutral medium via intramolecular reaction of cycloaddition. As a result of protonation and 1,6 – closure, dihydronaphthalene derivative 5 was obtained as main product in the acidic medium. As a consequence of 10π electrocyclization reaction, a phenanthrene derivative 2 was obtained in a neutral and acid medium. Secondary 6π electrocyclization of fotoproduct 2 leads to pyrene compound 4, isolated only under reduced pH. All products were isolated and completely characterized by spectroscopic methods.

• Keywords: fotokemija; furan; o-divinilbenzen; elektrociklizacija; cikloadicija
• Keywords (english): photochemistry; furan; o-divinylbenzenes; electrocyclization; cycloaddition
• Language: croatian
• URN:NBN: urn:nbn:hr:149:923451
• Study programme: Title: Environmental Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka ekoinženjerstva (magistar/magistra inženjer/inženjerka ekoinženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-04-21 14:05:54