Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted ferrocenes
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted ferrocenes
Original language description
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.
Czech name
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Czech description
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Classification
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
Result continuities
Project
<a href="/en/project/GA18-10222S" target="_blank" >GA18-10222S: From simple precursors to unprecedented heterocyclic systems containing heavier Group 15 elements</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
New Journal of Chemistry
ISSN
1144-0546
e-ISSN
1369-9261
Volume of the periodical
45
Issue of the periodical within the volume
38
Country of publishing house
GB - UNITED KINGDOM
Number of pages
12
Pages from-to
18171-18182
UT code for WoS article
000696589200001
EID of the result in the Scopus database
2-s2.0-85116433287