Selektivne Michaelove adicije brez topil

diplomsko delo

Filip Džeroski (Author), Marjan Jereb (Mentor)

Abstract

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.

Keywords

zelena kemija;organske reakcije;Michaelova adicija;reakcije brez topil;aktivirane metilenske spojine;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2022
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[F. Džeroski]
UDC:	547(043.2)
COBISS:	95233539
Views:	215
Downloads:	38
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Solvent-free selective Michael additions
Secondary 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.
Secondary keywords:	Michael addition;solvent-free;green chemistry;activated methylene compounds;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	48 str.
ID:	14363934