Title
Ispitivanje reakcija građenja acetala pomoću trifenilfosfina i ugljen-tetrahlorida i oksidativnim aminovanjem metil-ketona pomoću joda i amina
Creator
Nešić, Milan, 1991-
CONOR:
109082889
Copyright date
2023
Object Links
Select license
Autorstvo-Nekomercijalno-Bez prerade 3.0 Srbija (CC BY-NC-ND 3.0)
License description
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Language
Serbian
Cobiss-ID
Theses Type
Doktorska disertacija
description
Datum odbrane:
Other responsibilities
Academic Expertise
Prirodno-matematičke nauke
Academic Title
-
University
Univerzitet u Nišu
Faculty
Prirodno-matematički fakultet
Group
Odsek za hemiju
Alternative title
Investigation of acetal formation effectuated by triphenylphosphine and carbon tetrachloride, and oxidative amination of methyl ketones by iodine and amines
Publisher
[M. Nešić]
Format
794 str.
description
Biografija sa bibliografijom: str. 790-794
Bibliografija: str. 790-794.
description
Organic chemistry and biochemistry, organic synthesis
Abstract (en)
The aim of this doctoral dissertation was the development of a new method for the synthesis of acetals using a combination of reagents PPh3 and CCl4, directly from aldehydes and stoichiometric amounts of alcohol, under neutral conditions. This reagent combination was also used for the synthesis of tetrahydrofuranyl acetals of structurally different alcohols, using autoxidized tetrahydrofuran. In the second part, a facile one-step oxidative introduction of three nitrogen atoms onto arylmethyl ketones was developed yielding α-iminoamidines, a functionality completely unknown to chemistry. Depending on the fine-tuning of the reaction conditions, reaction workup, or simple subsequent transformations, this synthetic approach led to other nitrogen-containing compounds thus greatly broadening the structural diversity introduced in this way. A physico-chemical characterization of the products revealed that α-iminoamidines display biologically important properties such as a tunable combination of basicity and lipophilicity, and a possibility to be further diversified in a stereochemical manner via axial stereoisomerism. All synthesized products (acetals and α-iminoamidines) were fully spectrally (1D and 2D NMR, IR and MS) characterized, and their NMR spectra were assigned through the analysis of 1D and 2D NMR spectra. The spectrum assignment of the synthesized diastereomeric acetals and α-iminoamidines was performed directly from the mixture by spin simulation, that is, by generating the spectrum of the mixture by summing the simulated 1H NMR spectra of the individual diastereomers, and comparing it with the recorded spectra. In cases where it is necessary, spin simulation was also used for the assignment of spectra of other products. A detailed analysis of the NMR spectra of the prepared α-iminoamidines was conducted to investigate the presence of slow conformational processes and chemical exchanges.
Authors Key words
Acetali, trifenilfosfin, ugljen-tetrahlorid, amin, jod, α-iminoamidin, acetofenon, 2-metilketon, organska sinteza, hromatografija
Authors Key words
Acetals, triphenylphosphine, carbon tetrachloride, amine, iodine, α-iminoamidine, acetophenone, 2-methylketone, organic synthesis, chromatography
Classification
581.192:582.998.16(043.3)
547-316:[546.181.1+547.412.113
547-316:[547.594
Subject
P 003, P 390, P 351, P 300
Type
Tekst
Abstract (en)
The aim of this doctoral dissertation was the development of a new method for the synthesis of acetals using a combination of reagents PPh3 and CCl4, directly from aldehydes and stoichiometric amounts of alcohol, under neutral conditions. This reagent combination was also used for the synthesis of tetrahydrofuranyl acetals of structurally different alcohols, using autoxidized tetrahydrofuran. In the second part, a facile one-step oxidative introduction of three nitrogen atoms onto arylmethyl ketones was developed yielding α-iminoamidines, a functionality completely unknown to chemistry. Depending on the fine-tuning of the reaction conditions, reaction workup, or simple subsequent transformations, this synthetic approach led to other nitrogen-containing compounds thus greatly broadening the structural diversity introduced in this way. A physico-chemical characterization of the products revealed that α-iminoamidines display biologically important properties such as a tunable combination of basicity and lipophilicity, and a possibility to be further diversified in a stereochemical manner via axial stereoisomerism. All synthesized products (acetals and α-iminoamidines) were fully spectrally (1D and 2D NMR, IR and MS) characterized, and their NMR spectra were assigned through the analysis of 1D and 2D NMR spectra. The spectrum assignment of the synthesized diastereomeric acetals and α-iminoamidines was performed directly from the mixture by spin simulation, that is, by generating the spectrum of the mixture by summing the simulated 1H NMR spectra of the individual diastereomers, and comparing it with the recorded spectra. In cases where it is necessary, spin simulation was also used for the assignment of spectra of other products. A detailed analysis of the NMR spectra of the prepared α-iminoamidines was conducted to investigate the presence of slow conformational processes and chemical exchanges.
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