Sinteza acilnih derivata furo-benzobiciklo[3.2.1]oktadienskog fotoprodukta

undergraduate thesis

• Title (english): Synthesis of acyl derivatives of the furo-benzobicyclo[3.2.1]octadiene photoproduct
• Author: Marin Smoljo
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Marijana Kraljić Roković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-17, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U svrhu funkcionalizacije benzobiciklo[3.2.1]oktadienskog skeleta provedene su reakcije Friedel-Craftsovog aciliranja. Početni spoj 1 priređen je Wittigovom reakcijom u obliku smjese cis- i trans-izomera te podvrgnut fotokemijskoj reakciji [2+2]-cikloadicije, pri čemu je dobiven spoj 2 koji u strukturi sadrži benzobiciklo[3.2.1]oktadiensku i furansku podjedinicu. Na spoju 2 provedene su reakcije Friedel-Craftsovog aciliranja različitim kiselinskim kloridima, pri čemu su sintetizirani spojevi 3-11. Reakcije su provedene u prisutnosti aluminijevog klorida, AlCl3 kao katalizatora, a kao otapalo su se koristili diklormetan (za spojeve 3, 4, 5, 6, 6a i 7) i kloroform (za spojeve 8, 9, 10 i 11). Kod svih provedenih procedura te dobivenih spojeva došlo je do otvaranja furanskog prstena tijekom reakcije aciliranja. Svi sintetizirani spojevi 3-11 okarakterizirani su spektroskopskom metodom 1H NMR.

Abstract (english)

For the purpose of functionalization benzobicyclo[3.2.1]octadiene skeleton, Friedel-Crafts acylations were performed. Starting compound 1 was obtained as mixture of cis- and trans- isomers by the Wittig reaction. [2+2]-photocycloaddition was carried out on starting compound 1 and compound 2, which contains benzobicyclo[3.2.1]octadiene skeleton and the furan ring, was obtained. Compound 2 was subjected to the Friedel-Crafts acylations with a series of acyl chlorides. In these reactions new 3-11 derivatives were synthesized. Reactions were carried out in dichloromethane (for compounds 3, 4, 5, 6, 6a i 7) and chloroform (for compounds 8, 9, 10 i 11) as a solvents, with aluminium chloride (AlCl3) as a catalyst. All reactions resulted in the ring opening of furan. All synthesized derivatives 3-11 were characterized by spectroscopic method 1H NMR.

• Keywords: benzobiciklo[3.2.1]oktadien; Friedel-Craftsovo aciliranje; fotokemijska cikloadicija; furan; kiselinski kloridi; aluminijev klorid
• Keywords (english): benzobicyclo[3.2.1]octadiene; Friedel-Crafts acylation; photochemical cycloaddition; furan; acyl chlorides; aluminium chloride
• Language: croatian
• URN:NBN: urn:nbn:hr:149:108406
• Study programme: Title: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-05-29 08:16:38