magistrsko delo
Grega Kos (Author), Krištof Kranjc (Mentor), Mitja Kolar (Thesis defence commission member), Uroš Grošelj (Thesis defence commission member)

Abstract

V prvi fazi magistrskega dela sem sintetiziral serijo biciklo[2.2.2]oktenov iz primerno substituiranih 2H-piran-2-onov ter maleimida. Reakcije so potekale v skladu s pričakovanji dobro poznanih Diels–Alderjevih cikloadicij. Pripravljeni biciklo[2.2.2]okteni so predstavljali izhodne spojine v naslednji stopnji, t.j. reakciji N-halogeniranja, kjer sem želel ustvariti vez med halogenom (klorom) ter obročnim dušikovim atomom. Z modifikacijo postopkov iz literature sem tako razvil okolju prijazno N-kloriranje. Uporabil sem NaCl, ki je bil vir klora, oksidant okson, trdni Al2O3 ter kloroform kot topilo. Reakcije sem izvajal v zaprti ACE cevki pri temperaturi 45 °C, s spreminjanjem reakcijskih pogojev sem na ta način uspešno pripravil tri nove N,N'-dikloro derivate pripojenih biciklo[2.2.2]oktenskih sistemov. V drugi fazi eksperimentalnega dela sem poizkusil iz predhodno sintetiziranih N-halogeniranih biciklo[2.2.2]oktenov in ustreznih piridinskih derivatov pripraviti kokristale, ki bi vsebovali halogensko vez. Za ta namen sem kot akceptorja halogenske vezi uporabil 2,2'-bipiridil ter 4,4'-bipiridil, kar bi omogočilo nadaljnje raziskave narave halogenske vezi. Žal priprava kristalov ni uspela.

Keywords

derivati pirana;piranoni;2H-piran-2-oni;cikloadicije;Diels-Alderjeva reakcija;halogenirani biciklo[2.2.2]okteni;halogenska vez;kokristali;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [G. Kos]
UDC: 547.81:66.094.41(043.2)
COBISS: 22864131 Link will open in a new window
Views: 506
Downloads: 211
Average score: 0 (0 votes)
Metadata: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Other data

Secondary language: English
Secondary title: Synthesis of bicyclo[2.2.2]octenes from various 2H-pyran-2-ones and maleimide or its derivatives as a basis for investigating halogen bonding
Secondary abstract: In the first phase of my master's thesis, I synthesized a variety of bicyclo[2.2.2]octenes from suitably substituted 2H-pyran-2-ones and maleimide. The reactions were took place according to the well known Diels–Alder cycloadditions. The prepared bicyclo[2.2.2]octenes represented the starting reactant in the following step of N-halogenation reaction where I tried to form a bond between a halogen (chlorine) and a ring nitrogen. By appropriate modifications of the literature reaction conditions, I developed environmentally friendly N-chlorination, using NaCl, which was the source of chlorine, oxone as the oxidant, solid Al2O3, and chloroform as the solvent. The reactions were carried out in closed ACE tubes at 45 °C. By changing the reaction parameters I managed to successfully synthesize three new N,N'-dichloro derivatives of fused bicyclo[2.2.2]octene systems. In the second phase of the experimental work, I tried to prepare co-crystals from previously synthesized N-halogenated bicyclo[2.2.2]octenes and suitable pyridine derivatives, which would presumably contain halogen bond, using 2,2'-bipyridyl and 4,4'-bipyridyl, as the halogen bond acceptors. Preparation of such crystals would allow further investigations into the nature of halogen bonding. Unfortunately, the preparation of the crystals was not successful.
Secondary keywords: 2H-pyran-2-ones;Diels-Alder reaction;halogenated bicyclo[2.2.2]octenes;halogen bond;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo
Pages: XI f., 60 str.
ID: 11888312