Method for the Synthesis of Ferrocenylhydrazine and Its Properties and Reactivity

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Method for the Synthesis of Ferrocenylhydrazine and Its Properties and Reactivity

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Method for the Synthesis of Ferrocenylhydrazine and Its Properties and Reactivity

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

<a href="/cs/project/GA21-02964S" target="_blank" >GA21-02964S: Dusíkaté ligandy pro prvky nepřechodných kovů - objemnější, konjugovanější a reaktivnější</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Organometallics

ISSN

0276-7333

e-ISSN

1520-6041

Svazek periodika

42

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

2405-2414

Kód UT WoS článku

001184395400001

EID výsledku v databázi Scopus

2-s2.0-85171558458