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The new catalytic method for the synthesis of 1-boryl-4-metalloid(Si, Ge, B)butadienes and other derivatives of 1-borylbutadienes

Jadwiga Pyziak

Abstract

The main aim of the study presented within the doctoral dissertation was to establish the reactivity of ethynylmetalloides (ethynylgermananes, ethynylboranes, alkynes with different functional groups) in the co-dimerization reaction. The products obtained, owing to the presence of the same or different metalloids in extreme positions of their molecules were expected to be interesting reagents for organic synthesis. The reactivity of diethynylsubstituted alkynes, silyl and germylalkynes, which until now has not been tested in this type of reactions, was also checked. Another challenge of the study was functionalization of ethynylsiloxysilsesquioxanes, cage organosilicon compounds of hybrid inorganic-organic properties, which was expected to permit the introduction of a borylobutadienyl group into the structure of these compounds. Detailed mechanistic studies, based on the density functional theory methods (DFT) were performed and kinetic measurements were made for the model coupling reaction of terminal silil-, boryl- and germylsubstituted alkynes with vinylboronates, which permitted determination of the rate limiting step of the process. These studies confirmed the results of experimental work for the stoichiometric reaction of sililalkynes with vinylboronates, for which the mechanism has been developed. In addition, mechanistic studies were extended to a number of other reactions with equimolar ethynylgermananes, to contribute to full understanding of the chemistry of this process.
Record ID
UAMa36790e3903e46d890626e4c9c33df6c
Diploma type
Doctor of Philosophy
Author
Jadwiga Pyziak Jadwiga Pyziak,, Centrum Zaawansowanych Technologii (Cb/CZT)Centra badawcze [nowa struktura organizacyjna] (Cb)
Title in Polish
Nowa katalityczna metoda syntezy 1-borylo-4-metaloido(Si,Ge,B)-butadienów oraz innych pochodnych 1-borylobutadienów
Title in English
The new catalytic method for the synthesis of 1-boryl-4-metalloid(Si, Ge, B)butadienes and other derivatives of 1-borylbutadienes
Language
pol (pl) Polish
Certifying Unit
Faculty of Chemistry (SNŚ/WC/FoC) [Not active]
Discipline
chemistry / (chemical sciences domain) / (physical sciences)
Status
Finished
Year of creation
2015
Start date
16-06-2015
Defense Date
16-06-2015
Title date
16-06-2015
Supervisor
URL
https://hdl.handle.net/10593/13279 Opening in a new tab
Keywords in English
1-borylobutadieny,1-borylbutadienes,kinetic studies; 3-dienes; DFT calculations
Abstract in English
The main aim of the study presented within the doctoral dissertation was to establish the reactivity of ethynylmetalloides (ethynylgermananes, ethynylboranes, alkynes with different functional groups) in the co-dimerization reaction. The products obtained, owing to the presence of the same or different metalloids in extreme positions of their molecules were expected to be interesting reagents for organic synthesis. The reactivity of diethynylsubstituted alkynes, silyl and germylalkynes, which until now has not been tested in this type of reactions, was also checked. Another challenge of the study was functionalization of ethynylsiloxysilsesquioxanes, cage organosilicon compounds of hybrid inorganic-organic properties, which was expected to permit the introduction of a borylobutadienyl group into the structure of these compounds. Detailed mechanistic studies, based on the density functional theory methods (DFT) were performed and kinetic measurements were made for the model coupling reaction of terminal silil-, boryl- and germylsubstituted alkynes with vinylboronates, which permitted determination of the rate limiting step of the process. These studies confirmed the results of experimental work for the stoichiometric reaction of sililalkynes with vinylboronates, for which the mechanism has been developed. In addition, mechanistic studies were extended to a number of other reactions with equimolar ethynylgermananes, to contribute to full understanding of the chemistry of this process.
Thesis file
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Uniform Resource Identifier
https://researchportal.amu.edu.pl/info/phd/UAMa36790e3903e46d890626e4c9c33df6c/
URN
urn:amu-prod:UAMa36790e3903e46d890626e4c9c33df6c

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