Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted ferrocenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F21%3A39921506" target="_blank" >RIV/00216275:25310/21:39921506 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2021/nj/d1nj02666f" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2021/nj/d1nj02666f</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d1nj02666f" target="_blank" >10.1039/d1nj02666f</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted ferrocenes

Popis výsledku v původním jazyce

The reaction of acetylferrocene hydrazone or 1,10-diacetylferrocene dihydrazone with PCl3 gives thecorresponding azines as the only organometallic product. The separation of the hydrazone function with a 1,4-phenylene or propane-2,2-diyl spacer enables the preparation of new heterocyclic compounds [(2H-1,2,3-diazaphosphol-5-yl)-4-phenyl]ferrocene (2b) and [1-(2H-1,2,3-diazaphosphol-5-yl)-1-methyl-ethyl]ferrocene(2c) but in low yields. Using acetylated hydrazones, that do not undergo transformation into stable azinemolecules, led to the synthesis of (2-acetyl-1,2,3-diazaphosphol-5-yl)ferrocene (5a) and 1,10-bis(2-acetyl-1,2,3-diazaphosphol-5-yl)ferrocene (8) in up to 70% yield. N-Acylated compounds 5a and 8 are readilyconverted to (2H-1,2,3-diazaphosphol-5-yl)ferrocene (2a) and 1,10-bis(2H-1,2,3-diazaphosphol-5-yl)ferrocene(9). Analogous reactions were utilized for the preparation of (2-acetyl-1,2,3-diazarsol-5-yl)ferrocene (10), (2H-1,2,3-diazarsol-5-yl)ferrocene (11), 1,10-bis(2-acetyl-1,2,3-diazarsol-5-yl)ferrocene (12) and 1,10-bis(2H-1,2,3-diazarsol-5-yl)ferrocene (13). Electrochemical studies on a series of new ferrocenes showed that the2H-1,2,3-diazapnictol-5-yl substituent possesses weak electron-withdrawing ability which is enhanced byacetylation in the 2-position of such a heterocycle. We also observed the electroactivity of the 1,2,3-diazapnictolyl substituent as it could be irreversibly reduced at potentials from 1.97 to 2.93 V vs. the Fc0/+couple. All prepared compounds have been fully characterized using spectroscopic methods and molecularstructures of 2a, 2b, 2c, 5a, 8, 9 and 10 are reported.

Název v anglickém jazyce

Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted ferrocenes

Popis výsledku anglicky

The reaction of acetylferrocene hydrazone or 1,10-diacetylferrocene dihydrazone with PCl3 gives thecorresponding azines as the only organometallic product. The separation of the hydrazone function with a 1,4-phenylene or propane-2,2-diyl spacer enables the preparation of new heterocyclic compounds [(2H-1,2,3-diazaphosphol-5-yl)-4-phenyl]ferrocene (2b) and [1-(2H-1,2,3-diazaphosphol-5-yl)-1-methyl-ethyl]ferrocene(2c) but in low yields. Using acetylated hydrazones, that do not undergo transformation into stable azinemolecules, led to the synthesis of (2-acetyl-1,2,3-diazaphosphol-5-yl)ferrocene (5a) and 1,10-bis(2-acetyl-1,2,3-diazaphosphol-5-yl)ferrocene (8) in up to 70% yield. N-Acylated compounds 5a and 8 are readilyconverted to (2H-1,2,3-diazaphosphol-5-yl)ferrocene (2a) and 1,10-bis(2H-1,2,3-diazaphosphol-5-yl)ferrocene(9). Analogous reactions were utilized for the preparation of (2-acetyl-1,2,3-diazarsol-5-yl)ferrocene (10), (2H-1,2,3-diazarsol-5-yl)ferrocene (11), 1,10-bis(2-acetyl-1,2,3-diazarsol-5-yl)ferrocene (12) and 1,10-bis(2H-1,2,3-diazarsol-5-yl)ferrocene (13). Electrochemical studies on a series of new ferrocenes showed that the2H-1,2,3-diazapnictol-5-yl substituent possesses weak electron-withdrawing ability which is enhanced byacetylation in the 2-position of such a heterocycle. We also observed the electroactivity of the 1,2,3-diazapnictolyl substituent as it could be irreversibly reduced at potentials from 1.97 to 2.93 V vs. the Fc0/+couple. All prepared compounds have been fully characterized using spectroscopic methods and molecularstructures of 2a, 2b, 2c, 5a, 8, 9 and 10 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/GA18-10222S" target="_blank" >GA18-10222S: Od jednoduchých prekurzorů k unikátním heterocyklům obsahující těžší prvky 15. skupiny</a><br>

Návaznosti

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

Rok uplatnění

2021

Kód důvěrnosti údajů

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

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

1369-9261

Svazek periodika

45

Číslo periodika v rámci svazku

38

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

18171-18182

Kód UT WoS článku

000696589200001

EID výsledku v databázi Scopus

2-s2.0-85116433287