Diels–Alderjeve cikloadicije cikličnih alkenskih dienofilov na substituirane 2H-piran-2-one v okolju in človeku prijaznejših topilih

Drofenik, Neža (author), Kranjc, Krištof (mentor)

Različno substituirani 3-benzoilamino-2H-piran-2-oni z Diels–Alderjevo cikloadicijo z maleinahidridom ali N-fenilmaleimidom vodijo v nastanek biciklo[2.2.2]oktenskih sistemov. V svojem magistrskem delu opisujem izvedbo omenjenih reakcij v topilih, ki jih je možno pridobivati iz biomase. Takšna topila predstavljajo eno izmed novejših vrst topil, ki se uvrščajo pod zeleno kemijo. Uspešno sem sintetizirala več različno substituiranih biciklo[2.2.2]oktenskih produktov v para-cimenu, α-pinenu in evkaliptolu. V para-cimenu sem tudi preizkusila in optimizirala nekatere reakcije, da bi dosegale čim višje konverzije, bile čim manj energijsko potratne in tako čim bolje ustrezale principom zelene kemije. Omenjene Diels–Alderjeve reakcije sem preizkusila tudi v limonenu, kjer reakcija ni potekla, in γ-valerolaktonu, kjer so bile težave z izolacijo produkta. Produkte, ki so uspešno nastali, sem okarakterizirala s pomočjo IR, 1H NMR in MS analize.

• Language: Slovenian
• Keywords: Diels–Alderjeve cikloadicije, biciklo[2.2.2]oktenski sistemi, zelena kemija, topila iz biomase
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-139141
• COBISS.SI-ID: 123531011
• Publication date in RUL: 31.08.2022

Secondary language

• Language: English
• Title: Diels–Alder cycloaddition of cyclic alkenes as dienophiles on substituted 2H-pyran-2-ones in solvents less hazardous to human health and the environment

Abstract

Various substituted 3-benzoylamino-2H-pyran-2-ones lead to bicyclo[2.2.2]octene derivatives upon reaction with maleic anhydride or N-phenylmaleimide via Diels–Alder cycloaddition. In this master's thesis, such reactions are described in biomass-derived solvents. This type of solvent is one of the newer types of green solvents. Various substituted bicyclo[2.2.2]octenes were synthesized in para-cymene, α-pinene and eucalyptol. Some of the reactions carried out in para-cymene were optimized to achieve high conversion rates, to be as energy efficient as possible, and to satisfy as many principles of green chemistry as possible. The aforementioned synthesis of bicyclo[2.2.2]octenes was also attempted in limonene, where the reaction did not occur and in γ-valerolactone, where problems with the isolation of the product were encountered. The successfully synthesized products were characterized by IR, 1H NMR and MS analytical methods.

• Keywords: Diels–Alder cycloaddition, bicyclo[2.2.2]octenes, green chemistry, biomass-derived solvents