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Sinteza biciklo[2.2.2]oktenov iz različnih 2H-piran-2-onov ter maleimida oziroma njegovih derivatov kot osnova za raziskovanje halogenskih vezi
Kos, Grega (Author), Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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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.

Language:Slovenian
Keywords:2H-piran-2-oni, Diels–Alderjeva reakcija, biciklo[2.2.2]okteni, halogenirani biciklo[2.2.2]okteni, halogenska vez.
Work type:Master's thesis/paper (mb22)
Tipology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
COBISS.SI-ID:22864131 This link opens in a new window
Views:274
Downloads:172
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Secondary language

Language:English
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
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.

Keywords:2H-pyran-2-ones, Diels–Alder reaction, bicyclo[2.2.2]octenes, halogenated bicyclo[2.2.2]octenes, halogen bond.

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