Cyclophosphazenes tethered together via N-ring centres with ortho-, meta- and para-xylylene linkers

Benson, Mark A.; Boomishankar, Ramamoorthy; Wright, Dominic S.; Steiner, Alexander

doi:10.1016/j.jorganchem.2006.11.052

Cited by 12 publications

(23 citation statements)

References 20 publications

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“…The partial substitution reaction of 4 with excess pyrrolidine results in geminal pyrrolidinyl-substituted phosphazene (7).…”

Section: Discussionmentioning

confidence: 99%

“…2,6-Dioxa-14,18-diazatricyclo-[18⋅4⋅0⋅0 7,12 ]-tetracosa- 7,9,11,20,22,24(1)-hexaene 1, 2,6-dioxa-14, 19-diazatricyclo-[19⋅4⋅0⋅0 7,12 ]-pentacosa- 7,9,11,21,23,25(1)-hexaene 2 and 2,7-dioxa-15,19-diazatricyclo-[19⋅4⋅0⋅0 8,13 ]-pentacosa-8, 10, 12, 21, 23, 25(1)-hexaene 3 40,41 were prepared according to the cited procedures. Also compound 4 was obtained from the reaction of 1 with N 3 P 3 Cl 6 according to the reported method.…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

“…[6][7][8][9] The different substituents that are bonded to phosphorus atoms are very effective for the determination of the physical and chemical properties of new phosphazene derivatives and polyorganophosphazenes. [10][11][12] Hence, researchers have focused on the replacement reactions of halogen atoms of halophosphazenes by different nucleophiles, e.g.…”

Section: Introductionmentioning

confidence: 99%

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Phosphorus-nitrogen compounds: Part 15. Synthesis, anisochronism and the relationship between crystallographic and spectral data of monotopic spiro-crypta phosphazenes

et al. 2008

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The reactions of hexachlorocyclotriphosphazatriene, N 3 P 3 Cl 6 , with N 2 O 2 -donor type coronands,, respectively. The reaction of 4 with excess pyrrolidine leads to the formation of geminal. The 31 P-NMR spectra of 5 and 6 indicate that these compounds have anisochronism. The structures of 5, 6 and 7 were investigated by X-ray crystallography. For 7, the sums of the bond angles around the N atoms were 348⋅6(2)° and 349⋅7(2)° indicating that the N atoms have pyramidal configurations and are stereogenic. The relationship between the chemical shift values δP (spiro) and the Δ(P-N) (electron density transfer parameters) of 4, 5, 6, 7 and the analogous compounds as well as the relationship between the Δ(δP) values and the above mentioned Δ(P-N) are presented respectively. In addition, the relationship between the endocyclic NPN bond angles of these compounds and the 31 P-NMR chemical shifts of the spiro-phosphorus atoms were investigated. The spectroscopic and structural investigations of the compounds were made by elemental analyses, MS, FTIR, one-dimensional 1 H-, 13 C-, 31 P-NMR, DEPT and two-dimensional COSY, HETCOR, HMBC, homo-and heteronuclear correlation techniques.

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“…The partial substitution reaction of 4 with excess pyrrolidine results in geminal pyrrolidinyl-substituted phosphazene (7).…”

Section: Discussionmentioning

confidence: 99%

Section: Synthesis Of Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phosphorus-nitrogen compounds: Part 15. Synthesis, anisochronism and the relationship between crystallographic and spectral data of monotopic spiro-crypta phosphazenes

et al. 2008

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“…17). This gives the option to link phosphazene rings via both covalent and hydrogen bonds [67]. [KH] + contains a ring NH site that binds anions in either monodentate or, supported by an exocyclic NH group, in bidentate fashion q.…”

Section: Hydrogen Bondingmentioning

confidence: 99%

Supramolecular Structures of Cyclotriphosphazenes

Steiner

2008

Polyphosphazenes for Biomedical Applications

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“…For most reported hexachlorocyclotriphosphazene derivatives, all six chlorine atoms were substituted by the same side groups. If two or more different side chains are used for the modification of hexachlorocyclotriphosphazene, product mixtures of structural isomers and products with different side‐chain ratios are formed due to the poor regioselectivity of many of these reactions 18. In 1942, Bode et al found that the substitution of chlorine atoms by phenyl groups always took place pairwise at the same phosphorus atom 19.…”

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confidence: 99%

Liquid chromatography/electrospray time‐of‐flight mass spectrometry for the characterisation of cyclic phosphazenes

Veldboer

Schürmann

Vogel

et al. 2010

Rapid Comm Mass Spectrometry

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Cyclic phosphazenes with different substituents were synthesised and investigated by liquid chromatography (LC) and electrospray ionisation mass spectrometry (ESI-MS). Hexachlorocyclotriphosphazene was functionalised with aliphatic substituents as alcohols and amines, leading to product mixtures, which were subsequently analysed. In contrast to classical methods of structural analysis such as nuclear magnetic resonance (NMR) spectroscopy or X-ray crystallography, which are restricted to pure compounds, these complex mixtures can favourably be analysed by means of LC/ESI-MS. The main products could be separated from by-products and, moreover, all the components of the unknown mixture were unambiguously identified by accurate mass measurements. For all compounds with different side-chain ratios, remaining chlorine atoms or hydroxyl groups and even for spiro or ansa products, molecular structures could be suggested.

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Cyclophosphazenes tethered together via N-ring centres with ortho-, meta- and para-xylylene linkers

Cited by 12 publications

References 20 publications

Phosphorus-nitrogen compounds: Part 15. Synthesis, anisochronism and the relationship between crystallographic and spectral data of monotopic spiro-crypta phosphazenes

Phosphorus-nitrogen compounds: Part 15. Synthesis, anisochronism and the relationship between crystallographic and spectral data of monotopic spiro-crypta phosphazenes

Supramolecular Structures of Cyclotriphosphazenes

Liquid chromatography/electrospray time‐of‐flight mass spectrometry for the characterisation of cyclic phosphazenes

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