Method for the Synthesis of Ferrocenylhydrazine and Its Properties and Reactivity

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F23%3A39921507" target="_blank" >RIV/00216275:25310/23:39921507 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acs.organomet.3c00332?ref=PDF" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.organomet.3c00332?ref=PDF</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.organomet.3c00332" target="_blank" >10.1021/acs.organomet.3c00332</a>

Result language
angličtina
Original language name
Method for the Synthesis of Ferrocenylhydrazine and Its Properties and Reactivity
Original language description
The reaction of iodoferrocene (FcI) with tert-butyl orbenzyl carbazate gives the protected ferrocenylhydrazines tert-butyl-1-ferrocenylhydrazine-1-carboxylate (1) and benzyl-1-ferrocenylhydrazine-1-carboxylate (2). Air-stable 2 was converted to ferrocenylhydrazine(3) by Pd-catalyzed hydrogenolysis under mild conditions inyields of up to 70% (based on the starting FcI). The applicability of 3in the synthesis of heterocycles bearing a Fc−N−N fragment wasdemonstrated by the preparation of (3,5-dimethylpyrazol-1-yl)ferrrocene (4), (3-trifluoromethyl-5-phenyl-pyrazol-1-yl) ferrrocene(5), (1,2,4-diazaphosphol-1-yl) ferrrocene (6), (1,2,4-diazarsol-1-yl)ferrrocene (7), and 1-ferrocenyl-4,5-dichloro-pyridazin-6-one (8).Condensation of 3 with FcCHO yielded bimetallic ferrocenecarboxaldehyde ferrocenylhydrazone (9). Electrochemical studies onthis series of ferrocenylated compounds showed that both thehydrazine and protected hydrazine function serve as electron donors, whereas N-bonded heterocycles possess weak electronwithdrawingproperties. All compounds studied have been fully characterized by spectroscopic methods and their molecularstructures are reported.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10402 - Inorganic and nuclear chemistry

Project
<a href="/en/project/GA21-02964S" target="_blank" >GA21-02964S: Nitrogen Ligands for Main-Group Elements - Becoming Bulkier, More Conjugated and Guilty</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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