Chemistry of diphenyltetrafluorophosphazene: Reactions with dilithiated diols

Elias, Anil J.; Muralidharan, K.; Kumar, M. Senthil; Venugopalan, Paloth

doi:10.1016/j.jfluchem.2006.05.001

Cited by 7 publications

(2 citation statements)

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“…Cyclophosphazene and poly(organo)phosphazene derivatives, which exhibit a variety of different functional groups and contain alternate P and N atoms in their cyclic and linear backbones, are an important family of inorganic systems. , It is well-known that ferrocene and its derivatives are very important compounds for photochemistry − and modern organometallic chemistry because of their outstanding stabilities, generating novel materials possessing interesting chemical, electrical, optical, and magnetic properties. , A scan of the literature shows that ferrocenylphosphazene derivatives are very limited. , The involvement of ferrocene derivatives with the phosphazene ring is also limited to monofunctional reagents for the preparation of electroactive ferrocenylphosphazenes , and dendrimers . To the best of our knowledge, there are no reports on the reactions of ferrocenyldiamines with N 3 P 3 Cl 6 in the literature.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus−Nitrogen Compounds. 18. Syntheses, Stereogenic Properties, Structural and Electrochemical Investigations, Biological Activities, and DNA Interactions of New Spirocyclic Mono- and Bisferrocenylphosphazene Derivatives

et al. 2009

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The reactions of hexachlorocyclotriphosphazatriene, N(3)P(3)Cl(6), with mono- (1 and 2) and bisferrocenyldiamines (3-5), FcCH(2)NH(CH(2))(n)NHR(1) (R(1) = H or FcCH(2)-), produce mono- (6 and 7) and spirocyclic bisferrocenylphosphazenes (8-10). The fully substituted phosphazenes (11-15 and 18-21) are obtained from the reactions of corresponding partly substituted phosphazenes (6-10) with excess pyrrolidine and NH(2)(CH(2))(3)ONa, respectively. The reactions of 6 with 1-aza-12-crown-4 afford geminal (16) and tris (17) crown ether-substituted phosphazenes. The structural investigations of the compounds have been verified by elemental analyses, mass spectrometry, Fourier transform IR, (1)H, (13)C, and (31)P NMR, and DEPT, COSY, HETCOR, and HMBC techniques. The crystal structures of 7, 10, 11, and 15 have been determined by X-ray crystallography. In 16 and 17, there are one and two stereogenic P atoms, respectively, and they are expected to be in enantiomeric mixtures. The structures of 18-21 look similar to a propeller. In 20 and 21, there are two stereogenic P atoms, and they exist as cis (meso; 20a and 21a) and trans (racemic; 20b and 21b) geometric isomers, according to the chiral solvating agent (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol experiments. Moreover, the compounds 18 and 19 have three stereogenic P atoms, and they exist as enantiomeric mixtures. Cyclic voltammetric investigations of compounds 6-21a reveal that ferrocene redox centers undergo oxidation concurrently at the same potential with basically reversible peaks, and these compounds appear to be quite robust electrochemically. The compounds 11-15 have been screened for antibacterial activity against gram positive and gram negative bacteria and for antifungal activity against yeast strains.The compounds 11, 12, 14, and 15 are evaluated for antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv (ATCC 27294). Interactions between compounds 11-15 and pBR322 plasmid DNA are studied by agarose gel electrophoresis. These compounds induce conformational changes in the DNA helix.

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Section: Introductionmentioning

confidence: 99%

Phosphorus−Nitrogen Compounds. 18. Syntheses, Stereogenic Properties, Structural and Electrochemical Investigations, Biological Activities, and DNA Interactions of New Spirocyclic Mono- and Bisferrocenylphosphazene Derivatives

et al. 2009

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“…On the other hand, mono and difunctional reagents were used for the preparations of electroactive ferrosenylphosphazenes by combining the phosphazene and ferrocene (Fc) rings. 13 So far, there have been three reports published by our group on the reactions of ferrocenyldiamines with OCCP . 12 b ,14 Meanwhile, a search of the literature revealed that there were several articles about spiro/ansa- cyclotetraphosphazenes containing 4-fluorobenzyl and Fc groups.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus–nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies

Elmas

Binici²,

Özgür

et al. 2022

New J. Chem.

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The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

Okumuş

Elmas

Kılıç

et al. 2021

Applied Organom Chemis

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In this study, two kinds of compounds, namely, mono‐ferrocenyl‐2‐cis‐4‐dichloro‐ansa‐ (2,4‐ansa; 3) and mono‐ferrocenyl‐spiro‐ (spiro; 4) hexachlorocyclotetraphosphazenes, were obtained by the Cl replacement reaction of N4P4Cl8 (1) with an equimolar amount of sodium 3‐(N‐ferrocenylmethylamino)‐1‐propanoxide (2). The reactions of 2,4‐ansa (3) with excess diamines and dialkoxides resulted in the formation of ansa‐cyclotetraphosphazenes (3a–3e). Spiro (4) was reacted with excess diamines and dialkoxides to give the mono‐ferrocenyl‐spiro‐cyclotetraphosphazenes (4a–4d). Although 2,4‐ansa (3) produced the dispiro (3a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine, it afforded both monospiro (3b) and dispiro (3c) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. However, spiro (4) yielded a trispiro (4a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine and 2,6‐dispiro (4b) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. The structures of the phosphazenes were elucidated by FTIR, ESI‐MS and/or HRMS, spectroscopic and crystallographic (for 3f and 4b) data. Furthermore, the electrochemical findings of cyclotetraphosphazenes exhibited electrochemically reversible one‐electron oxidation of Fe‐redox centre. As an example, the chirality of 3c was investigated by 31P NMR spectroscopy on the addition of (R)‐(+)‐2,2,2‐trifluoro‐1‐(9′‐anthryl)‐ethanol, chiral solvating agent (CSA). The circular dichroism (CD) (for 3d and 3e), HPLC (for 3d, 3e and 3f) and X‐ray (for 3f) display that these compounds have chirality (RS′ or SR′) in the solution and solid state. This paper also focuses on the antimicrobial activities, the interactions with pBR322 DNA, in vitro anticancer activity against L929 fibroblast and MCF7 breast cells, and antituberculosis activity against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.

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Chemistry of diphenyltetrafluorophosphazene: Reactions with dilithiated diols

Cited by 7 publications

References 23 publications

Phosphorus−Nitrogen Compounds. 18. Syntheses, Stereogenic Properties, Structural and Electrochemical Investigations, Biological Activities, and DNA Interactions of New Spirocyclic Mono- and Bisferrocenylphosphazene Derivatives

Phosphorus−Nitrogen Compounds. 18. Syntheses, Stereogenic Properties, Structural and Electrochemical Investigations, Biological Activities, and DNA Interactions of New Spirocyclic Mono- and Bisferrocenylphosphazene Derivatives

Phosphorus–nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies

The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

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