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Synthesis of annelated ferrocene compounds by C-H activation
Varmužová, Věra ; Štěpnička, Petr (advisor) ; Hrdina, Radim (referee)
Title: Synthesis of annelated ferrocene compounds by C-H activation Author: Věra Varmužová Department: Department of Inorganic chemistry Supervisor: prof. RNDr. Petr Štěpnička, Ph.D., DSc. Abstract: This diploma thesis disrcibes the synthesis of two annelated ferrocenes, ferroceno[c]isoquinoline (9) and benzo[f]ferroceno[c]isoquinoline (13). Starting compound used for their synthesis, [(methylsulfonyl)amino]ferrocene, was prepared from aminoferrocene. During the synthesis of compound 9, the reaction sequence was optimized, which includes the nucleophilic substitution, C-H activation and aromatization. Compound 13 was prepared similarly using the optimized reaction conditions An intermediate prepared during the synthesis of compound 9, 1,2-dihydro-2-(methylsulfonyl)ferroceno[c]isoquinoline (7), was additionally used to prepare cationic ruthenium complex 14, wherein it links as a η6 -ligand via its benzene ring. For compounds 7, 9 and 14 UV-VIS absorption spectra were recorded and compared. Key words: ferrocene, annelated ferrocenes, C-H activation, organometallic chemistry
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Synthesis and characterization of a phosphinoferrocene ligand modified by an amidosulfonate substituent
Varmužová, Věra ; Štěpnička, Petr (advisor) ; Gyepes, Róbert (referee)
Title: Synthesis and characterization of a phosphinoferrocene ligand modified by an amidosulfonate substituent Author: Věra Varmužová Department: Department of Inorganic chemistry Supervisor: prof. RNDr. Petr Štěpnička, Ph.D., DSc. Abstract: This bachelor thesis describes the synthesis of a new compound, 1-(diphenylphosphino)-1'-(methylsulfonamino)ferrocene (compound 2), from 1,1'-dibromoferrocene. Compound 2 was prepared by reaction of 1-(diphenylphosphino)-1'-aminoferrocene-borane (1: 1) with methanesulfonyl chloride in the presence of pyridine, followed by deprotection of the diphenylphosphine group. The conditions of the reaction were optimised so that the reaction was performed with complete consamption of the starting material. The synthesis proceeds via 1-(diphenylphosphino)-1'- (methylsulfonamino)ferrocene-borane (1: 1) (compound 2), which is also a new compound. Both compounds were characterised by nuclear magnetic resonance, mass spectroscopy, infrared spectroscopy, elemental analysis and their crystal structure was determined by single- crystal X-ray crystallography. Key words: ferrocene, phosphines, sulfonamides, synthesis.
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