Sinteza in pretvorbe elektronsko bogatih aromatov s halogenirnimi reagenti

Kobe, Robert (avtor), Jereb, Marjan (mentor)

V sklopu magistrskega dela sem raziskoval transformacije elektronsko bogatih aromatov z N-bromosukcinimidom (NBS) v 1,1,1,3,3,3-heksafluoroizopropanolu (HFIP). Prvi korak eksperimentalnega dela je priprava skupine elektronsko bogatih aromatov. Osnova za te spojine je 1,3,5-trimetoksibenzen, na katerega so vezane različne elektron-privlačne in elektron-donorske skupine. Nekaj takih spojin smo pridobili iz komercialnih virov in jih uporabili za nadaljnje transformacije. Sintetiziran set spojin sem funkcionaliziral z NBS in hkrati testiral HFIP kot reakcijski medij. Nastale produkte sem očistil in analiziral. Iz rezultatov sem ugotovil, kako struktura elektronsko bogatih aromatov vpliva na potek funkcionalizacije pod omenjenimi pogoji in kakšen vpliv imajo pri tem različni substituenti. Pozoren sem bil tudi na morebiten potek radikalskih in ostalih pretvorb.

• Jezik: Slovenski jezik
• Ključne besede: N-bromosukcinimid (NBS), 1, 1, 1, 3, 3, 3-heksafluoroizopropanol (HFIP), elektronsko bogati aromati, elektrofilne aromatske substitucije, 1, 3, 5-trimetoksibenzen.
• Vrsta gradiva: Magistrsko delo/naloga
• Tipologija: 2.09 - Magistrsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2025
• PID: 20.500.12556/RUL-174265
• COBISS.SI-ID: 258901763
• Datum objave v RUL: 30.09.2025

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Synthesis and transformations of electron rich aromatic compounds with halogenated reagents

Izvleček

The main goal of my master's thesis is studying transformations of electron rich aromatics with N-bromosuccinimide (NBS) in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). First step is the preparation of a set of electron rich aromatics. The basis for these compounds is 1,3,5-trimethoxybenzene, containing different electron-withdrawing and electron-donating groups. Some of these compounds were purchased beforehand and were used for further transformations. I then functionalized this set of synthesized compounds with NBS and at the same time tested HFIP as a reaction medium. I have purified and analysed all products. Using the results I found out, how the structure of electron rich aromatics influences functionalization under such reaction conditions and what is the effect of different substituents. I also kept an eye out for possible radical and other transformations.

• Ključne besede: N-bromosuccinimide (NBS), 1, 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), electron rich aromatics, electrophilic aromatic substitutions, 1, 3, 5-trimethoxybenzene.