Termičke transformacije 3- i 4-[4-(2-vinifenil)buta-1,3-dienil]piridina

undergraduate thesis

• Title (english): Thermal transformations of 3- and 4-[4-(2-vinylphenyl)buta-1,3-dienyl]pyridine
• Author: Josipa Hodak
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Ivana Šagud (član povjerenstva)
• Committee member: Jelena Macan (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2016-09-02, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U cilju proučavanja utjecaja heterocikličke jezgre kao supstituenta na termičko ponašanje konjugiranih butadienskih sustava, korišteni su novi piridinski derivati butadiena, 3-[4-(2-vinilfenil)buta-1,3-dienil]piridin (1) i 4-[4-(2-vinilfenil)buta-1,3-dienil]piridin (2). Spojevi 1 i 2 sintetizirani su Wittigovom reakcijom kao smjese geometrijskih izomera. Novosintetizirani derivati 1 i 2 podvrgnuti su termičkim reakcijama u različitim otapalima u cilju priprave novih bicikličkih struktura termičkim putem, te proučavanja reakcijskog mehanizma. Početni spojevi pokazali su različito termičko ponašanje te se pokazalo da je reakcija najučinkovitija u toluenu kao otapalu. Termička reakcija spoja 1 nije dovela do nastanka produkta u značajnom iskorištenju niti u jednom od korištenih otapala, dok termičkom reakcijom spoja 2 dolazi do (8π, 6π)-elektrociklizacije u biciklički produkt 4-[(2S,2aR,8bS-7)-1H,2H,2aH,3H,4H,8bH-ciklobuta[a]naftalen-2-il]piridin (7). Polazni spojevi 1 i 2 te produkt termičke reakcije 7, okarakterizirani su modernim spektroskopskim metodama, jednodimenzionalnim i dvodimenzionalnim NMR tehnikama.

Abstract (english)

In order to study the influence of heterocyclic nuclei as a substituent on the thermal behavior of the conjugated butadiene system, new pyridine derivatives of butadiene, 3- [4- (2-vinylphenyl)buta-1,3-dienyl]pyridine (1) and 4-[ 4-(2-vinylphenyl)buta-1,3-dienyl]pyridine (2), were prepared. They were synthesized by Wittig reaction as a mixture of geometric isomers. The newly synthesized derivatives 1 and 2 were subjected to thermal reactions in various solvents in the context of preparation of new bicyclic structures by reactions via thermal pathways and in order to investigate the reaction mechanism. The starting compounds showed different thermal behavior and it has been shown that the reaction goes best in toluene as solvent. Thermal reaction of the compound 1 did not entail a product in a significant yield in any solvent, while the thermal reaction of the compound 2 lead to (8π, 6π)-electrocyclic formation of the bicyclic product 4-[(2S,2aR,8bS-7)-1H,2H,2aH,3H,4H,8bH-cyclobuta[a]naphthalen-2-yl]pyridine (7). The starting compounds 1 and 2 and the thermal reaction product 7 have been characterized by modern spectroscopic methods, one-dimensional and two-dimensional NMR techniques.

• Keywords: termičke reakcije; (8π 6π)-elektrociklizacija; butadieni; piridinski derivati; spektroskopija
• Keywords (english): thermal reaction; (8π 6π)-electrocyclization; butadiene; pyridine derivatives; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:602286
• 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: 2018-01-30 12:40:04