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## Reductive amination reaction of 1,1'-diformyl-ferrocene

### Kamil Ziemkiewicz

#### Abstract

Organometallic chemistry is the study of chemical compounds containing at least one covalent bond between metal and carbon atom of an organic group. Organometallic compounds have found wide application in catalysis, as well as reagents in organic synthesis, they are important in the development of knowledge about chemical bonds and reaction mechanisms. Compounds containing a transition metal atom in their structure combined with two cyclopentadienyl ligands are commonly called metallocenes. The first discovered metallocene was ferrocene Fe(5-Cp)2, characterized by low toxicity and high potential for chemical modifications. For this reason, ferrocene derivatives are an interesting subject of research in terms of their biological activity. The aim of this work was to obtain full spectroscopic characteristics 1,1'-disubstituted ferrocene derivatives. The compounds were prepared by reductive amination reaction of 1,1'-diformyl-ferrocene with selected amino acid esters. As part of laboratory tests, I carried out the reactions of introducing the allyl group into mono-derivative ferrocene with glycine methyl ester. The first stage of my work was to obtain 1,1'-diformyl-ferrocene, methyl esters of glycine and L-alanine in the form of hydrochlorides based on known literature regulations. Next, I synthesized two new bis-derivatives of ferrocene 25 and 26 with yields of 51% and 60%, respectively. The obtained compounds were purified by means of SiO2 column chromatography and I performed a full 1H NMR, 13C NMR and MS spectroscopic analysis. I made an attempt to introduce an allyl group to a bis-derivative 25. I performed a reductive amination reaction of ferrocenecarboxaldehyde with glycine methyl ester to obtain compound 27 in a yield of 89%. The product was purified by SiO2 column chromatography and then subjected to 1H NMR analysis. The obtained compound served as a substrate in subsequent reactions with allyl bromide. I made two attempts to introduce an allyl group using different reaction conditions. I synthesized a new derivative 28 in 16% yield, which I characterized by means of 1H NMR and 13C NMR spectroscopy and MS. The reaction requires further optimization and the development of a new method to purify the resulting compound.
Diploma type
Engineer's / Bachelor of Science
Diploma type
Engineer's thesis
Author
Kamil Ziemkiewicz (FC) Kamil Ziemkiewicz,, Faculty of Chemistry (FC)
Title in Polish
Reakcje aminowania redukcyjnego 1,1'-diformyloferrocenu
Supervisor
Włodzimierz Buchowicz (FC/DOC) Włodzimierz Buchowicz,, Department Of Organic Chemistry (FC/DOC)Faculty of Chemistry (FC)
Certifying unit
Faculty of Chemistry (FC)
Affiliation unit
Department Of Organic Chemistry (FC/DOC)
Study subject / specialization
, Technologia Chemiczna
Language
(pl) Polish
Status
Finished
Defense Date
31-01-2019
Issue date (year)
2019
Reviewers
Wanda Ziemkowska (FC/DCOC) Wanda Ziemkowska,, Department Of Catalysis And Organometallic Chemistry (FC/DCOC)Faculty of Chemistry (FC) Włodzimierz Buchowicz (FC/DOC) Włodzimierz Buchowicz,, Department Of Organic Chemistry (FC/DOC)Faculty of Chemistry (FC)
Keywords in Polish
chemia metaloorganiczna, ferrocen, estry aminokwasów, aminowanie redukcyjne
Keywords in English
organometallic chemistry, ferrocene, amino acid esters, reductive amination
Abstract in Polish
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Identyfikator pracy APD: 30233

Uniform Resource Identifier
https://repo.pw.edu.pl/info/bachelor/WUT02cf853fe6c14e478fd4fe1cdd2e9311/
URN
urn:pw-repo:WUT02cf853fe6c14e478fd4fe1cdd2e9311

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