Funkcionalizacija benzobiciklo[3.2.1]oktadienskog skeleta reakcijama supstitucije

undergraduate thesis

• Title (english): Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via substitution reactions
• Author: Ivana Puček
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-10, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U cilju funkcionalizacije benzobiciklo[3.2.1]oktadienskog skeleta provedene su reakcije supstitucije, točnije Buchwald-Hartwigove reakcije. U tim reakcijama, supstitucijom na početnom klorovom derivatu endo-1 biciklo[3.2.1]oktadienske strukture, s nizom primarnih benzilnih amina, sintetizirani su novi derivati endo-2-16 i 17-19. Sve reakcije provedene su u dioksanu kao otapalu, s paladijem kao katalizatorom i BrettPhos ligandom, a korištena baza bila je kalijev tert-butoksid. Iskorištenje provedenih reakcija, između ostalog, ovisi o steričkim smetnjama koje su posljedica neplanarne strukture početnog spoja endo-1, te o vrsti i položaju supstituenta korištenog primarnog benzilnog amina. Očekivani derivati endo-2-16 nastali C-N unakrsnim povezivanjem nisu jedini izolirani spojevi. Uz njih, izolirani su i produkti 17-19 kod kojih je, osim očekivanog mehanizma reakcije, došlo i do alilnog pregrađivanja. Svi sintetizirani derivati endo-2-16 i 17-19 u potpunosti su okarakterizirani modernim spektroskopskim metodama.

Abstract (english)

For the purpose of functionalization benzobicyclo[3.2.1]octadiene skeleton, substitution reactions were performed, more precisely Buchwald-Hartwig's reaction. In these reactions, new endo-2-16 and 17-19 derivatives were synthesized by replacing the starting chlorine derivative on the bicyclo[3.2.1]octadiene derivative endo-1 with a series of primary benzylic amines. All reactions were carried out in dioxane as a solvent, with palladium as a catalyst and BrettPhos as a ligand, with potassium tert-butoxide as a base. The yields of the reactions, among other things, depends on the steric disturbances resulting from the nonplanar structure of the endo-1 starting compound, and on the type and position of the substituent used in the primary benzylic amine. Expected derivatives endo-2-16, which were obtained by C-N cross-coupling reactions are not the only isolated compounds. In addition, products 17-19 were isolated in which, apart from the expected reaction mechanism, also allylic rearrangement occurred. All synthesized derivatives endo-2-16 and 17-19 were fully characterized by modern spectroscopic methods.

• Keywords: sinteza amina; arilni kloridi; benzobiciklo[3.2.1]oktadieni; BrettPhos; Buchwald-Hartwigova aminacija
• Keywords (english): amine synthesis; aryl chloride; benzobicyclo[3.2.1]octadiene; BrettPhos; Buchwald-Hartwig amination
• Language: croatian
• URN:NBN: urn:nbn:hr:149:050723
• 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: 2021-11-22 11:05:37