Selektivne Michaelove adicije brez topil

Džeroski, Filip (author), Jereb, Marjan (mentor)

Pri svojem diplomskem delu sem se osredotočil na Michaelove adicije v prisotnosti in odsotnosti topil. Izvedel sem predvsem adicije aktiviranih metilenskih spojin (Michaelovi donorji) na tako α,β-nenasičene ketone kot tudi nitroalkene (Michaelovi akceptorji), in sicer v prisotnosti katalizatorjev LiClO4 in Et3N pri sobni temperaturi ter brez prisotnosti topil. Prav tako sem sintetiziral derivat rodanina v prisotnosti vode, a brez dodanih katalizatorjev. Reakcije sem najprej izvedel v manjšem merilu in jih kasneje izvedel še v večjem merilu, če so bile v manjšem merilu uspešne. Produkte reakcij v manjšem merilu sem izoliral z ekstrakcijo in destilacijo, pri reakcijah v večjem merilu pa sem produkte očistil s prekristalizacijo. Izkoristki reakcij v manjšem merilu so bili odlični, medtem ko so bili izkoristki pri večjem merilu slabi ali kvečjemu povprečni. Na koncu sem produkte analiziral z uporabo 1H NMR spektrov, ki sem jih posnel v CDCl3 pri 300 MHz.

• Language: Slovenian
• Keywords: Michaelova adicija, brez topil, zelena kemija, aktivirane metilenske spojine
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-134699
• COBISS.SI-ID: 95233539
• Publication date in RUL: 26.01.2022

DŽEROSKI, Filip, 2022, Selektivne Michaelove adicije brez topil [online]. Bachelor’s thesis. [Accessed 1 April 2025]. Retrieved from: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=eng&id=134699

Secondary language

• Language: English
• Title: Solvent-free selective Michael additions

Abstract

In the thesis, I focused on Michael additions in solution or under solvent-free conditions. I mostly carried out additions of activated methylene compounds (Michael donors) onto α,β-unsaturated ketone and nitroalkenes (Michael acceptors) in the presence of the LiClO4/Et3N catalyst at room temperature under solvent-free conditions. I also synthesized a rhodanine derivative in water under catalyst-free conditions. All reactions were first carried out on a smaller scale and later - if successful on the smaller scale - also on a larger scale. I isolated the small-scale products with extraction and distillation, while purification of products on a larger scale was performed by crystallization. Reactions on a smaller scale gave products in excellent yields, while large-scale reaction yields varied from poor to average. I analyzed my products using 1H NMR spectra recorded in CDCl3 at 300 MHz.

• Keywords: Michael addition, solvent-free, green chemistry, activated methylene compounds