Pretvorbe aktiviranih aromatov z N-halogenirnimi reagenti

magistrsko delo

Martin Podlipec (Author), Marjan Jereb (Mentor), Jurij Lah (Thesis defence commission member), Krištof Kranjc (Thesis defence commission member)

Abstract

V sklopu magistrskega dela sem sintetiziral serijo aktiviranih ketonov in alkoholov ter raziskoval njihove pretvorbe z N-halogenirnimi reagenti v alternativnem topilu 1,1,1,3,3,3-heksafluoroizopropanolu (HFIP). Pri reakcijah, kjer sem uporabil presežek N-bromosukcinimida (NBS) je hitreje poteklo bromiranje na aktiviranem mestu aromata (kot bi pričakovali pri elektrofilni aromatski substituciji) s sledečo počasnejšo ipso substitucijo. Pri ipso substituciji se je z obroča aktiviranega aromata odstranila že prisotna funkcionalna skupina in nastal je dvakrat bromiran produkt. Preučil sem vpliv strukture aromatskih spojin (aktiviranost in substituiranost aromatskega jedra, vpliv različno dolgih in razvejanih alkilnih verig) in vpliv različnih množin NBS na potek pretvorbe. Skušal sem izolirati tudi produkte, ki so vsebovali izstopajočo skupino ipso substitucije in morebitne druge stranske produkte. V nekaterih primerih mi je slednje uspelo in omogočilo širši vpogled v potek reakcije. Za boljše razumevanje pretvorb sem potek ene od reakcij spremljal z ¹H NMR spektroskopijo. Analiza rezultatov je potrdila prej opisan potek pretvorbe.

Keywords

N-bromosukcinimid;ipso substitucija;1,1,1,3,3,3-heksafluoroizopropanol;magistrska dela;

Data

Language:	Slovenian
Year of publishing:	2025
Typology:	2.09 - Master's Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[M. Podlipec]
UDC:	547.52:66.094.41(043.2)
COBISS:	243041027
Views:	88
Downloads:	36
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Transformations of activated aromatic compounds using N-halo reagents
Secondary abstract:	In my master’s thesis, I synthesized a number of activated ketones and alcohols and investigated their transformations using N-halogenating reagents in the alternative solvent 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). In reactions where an excess of N-bromosuccinimide (NBS) was used, rapid bromination occurred at the activated site of the aromatic compound, followed by a slower ipso substitution. During the ipso substitution step, the functional group was cleaved from the activated aromatic ring and replaced by a bromine atom, yielding a dibrominated aromatic product. I examined the influence of the aromatic compound structures (activation and substitution of the aromatic ring, effect of alkyl chain length and hindrance) as well as the effect of varying amounts of NBS on the transformation. Additionally, I isolated potential side products, which provided further insight into the reaction pathway. To gain a deeper understanding of the transformations, I monitored one of the reactions using ¹H NMR spectroscopy. The analysis of results confirmed the proposed reaction pathway.
Secondary keywords:	halogenation;N-bromosuccinimide;ipso substitution;1,1,1,3,3,3-hexafluoroisopropanol;Halogeniranje;Aromatske spojine;Univerzitetna in visokošolska dela;
Type (COBISS):	Master's thesis/paper
Study programme:	1000375
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages:	1 spletni vir (1 datoteka PDF (97 str.))
ID:	26719439