Sinteza substituiranih biciklo[2.2.2]oktenov s cikloadicijami med 2H-piran-2-onskimi derivati in maleinanhidridom ter nadaljnje pretvorbe z dušikovimi nukleofili
ID Pelko, Teja (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Z dvakratno Diels–Alderjevo reakcijo med derivati 2H-piran-2-onov in maleinanhidridom ali N-substituiranim maleimidom lahko pripravimo substituirane biciklo[2.2.2]oktene, pri čemer pride do eliminacije molekule CO2. Biciklo[2.2.2]oktenski derivati, ki vsebujejo maleinanhidridne obroče, so zanimive tarče za nadaljnje pretvorbe z dušikovimi nukleofili. V diplomskem delu naj bi bile raziskane reakcije, s katerimi bi na biciklični skelet uvedla piridinske in druge (hetero)aromatske amine, ki služijo bodisi kot ligandi za različne katione prehodnih kovin, bodisi kot akceptorji halogenske vezi in predstavljajo pomembne strukturne fragmente pri gradnji novih 2D in 3D molekulskih arhitektur.

Keywords:Diels–Alderjeva reakcija, 2H-piran-2-oni, biciklo[2.2.2]okteni, (hetero)aromatski amini, biciklični skelet
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
PID:20.500.12556/RUL-129225 This link opens in a new window
COBISS.SI-ID:75948291 This link opens in a new window
Publication date in RUL:30.08.2021
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Secondary language

Title:Synthesis of substituted bicyclo[2.2.2]octenes with cycloadditions between 2H-pyran-2-one derivatives and maleic anhydride and further transformations with nitrogen nucleophiles
By double Diels–Alder reaction of 2H-pyran-2-one derivatives and maleic anhydride or N-substituted maleimide, substituted bicyclo[2.2.2]octenes can be prepared via elimination of a CO2 molecule. Bicyclo[2.2.2]octene derivatives containing maleic anhydride rings are interesting targets for further conversions with nitrogen nucleophiles. In this Diploma work I intended to investigate reactions that would introduce pyridine and other (hetero)aromatic amines to the bicycle skeleton, which would serve either as ligands for various transition metal cations or as halogen bond acceptors and would thus represent important structural fragments in the construction of new 2D and 3D molecular architectures.

Keywords:Diels–Alder reaction, 2H-pyran-2-ones, bicyclo[2.2.2]octenes, (hetero)aromatic amines, bicycle skeleton

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