Flow fotokemija: primjena u sintezi benzobiciklo[3.2.1]-skeleta

undergraduate thesis

• Title (english): Flow photochemistry: application in the synthesis of the benzobicyclo[3.2.1]-skeleton
• Author: Patricia Debogović
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Sandra Babić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-18, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Praktična i jednostavna izvedba flow-fotokemijskog reaktora korištena je s ciljem učinkovitije sinteze benzobiciklo[3.2.1]oktadienskih produkata putem intramolekulske [2+2]-fotocikloadicije. Kao polazni spojevi korišteni su konjugirani butadienski derivati 1-8 s odgovarajućim supstituentima, sintetizirani Wittigovom reakcijom kao smjese cis- i trans- geometrijskih izomera. Takvi, novosintetizirani derivati podvrgnuti su fotokemijskom osvjetljavanju na 350 nm putem klasične (šaržne) i flow-metode. Uporabom šaržne metode sinteze dobiveni su fotoprodukti 1a-6b, dok primjenom flow-metode nastaju fotoprodukti 1a-4a. Vrijednosti iskorištenja, vremena reakcije kao i konverzije dobivene korištenjem flow-fotoreaktora uspoređivane su s vrijednostima dobivenima putem klasičnog, šaržnog fotoreaktora. U usporedbi sa šaržnim fotokemijskim reakcijama, flow-sinteze dale su bolje rezultate, kako u povećanju vrijednosti iskorištenja i produktivnosti, tako i u snižavanju vremena provođenja same reakcije. Ovo saznanje omogućava sintezu brojnih spojeva uporabom jednostavne i učinkovite laboratorijske opreme.

Abstract (english)

Practical and simple performance of flow photochemical reactor was used with a purpose of more efficient synthesis of benzobicyclo[3.2.1]octadiene products by intramolecular [2 + 2]- photocycloaddition reaction. As initial compounds there were used conjugated butadiene derivatives 1-8 with the corresponding supstituents, synthesized by Wittig's reaction as a mixture of cis- and trans-geometric isomers. Those, new synthesized derivates 1-6 were subjected to photochemical illumination at 350 nm by classical (batch) and flow method. By using the batch synthetic method, there were obtained the photoproducts 1a-6b. While using the flow method, there were produced the photoproducts 1a-4a. The values of yields, reaction times and conversions obtained by flow photoreactor were compared with the values obtained by a classical, batch photoreactor. In comparation with the batch photochemical synthesis, the flow photochemical reactions gave better results, greater values of yields and productivity and shorter reaction times. This knowledge enables the synthesis of numerous compounds using simple and efficient laboratory equipment.

• Keywords: šaržna fotokemijska sinteza; flow-fotokemija; Wittigova reakcija; benzobiciklo[3.2.1.]oktadienski fotoprodukti
• Keywords (english): batch photochemical synthesis; flow photochemistry; Wittig reaction; benzobicyclo[3.2.1]octadiene photoproducts
• Language: croatian
• URN:NBN: urn:nbn:hr:149:429896
• 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: 2022-05-17 13:41:45