Novel N-phosphorylated iminophosphoranes based on 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

Weinert, Michael; Fuhr, Olaf; Döring, Manfred

doi:10.24820/ark.5550190.p010.704

Cited by 4 publications

(4 citation statements)

References 27 publications

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“…Besides the previous researched Staudinger reaction as versatile tool in the synthesis of N-phosphorylated iminophosphoranes, 24,38 the possibility converting apparent pentavalent phosphorus compounds using the prototropic tautomeric equilibrium was confirmed. This reaction pathway opens up a new and convenient synthesis-pathway of bisphosphorylimides, leading to a tunable array of molecules with different phosphorus moieties.…”

Section: Discussionmentioning

confidence: 79%

“…Staudinger products out of phosphor azides do not show the same lability. 38 Thus the stability towards acidic hydrolysis of the synthesized product was tested in a simple NMR experiment exemplarily with two chosen compounds. DOPO-NH-DOPO and DPP-NH-DOPO were dissolved in acetonitrile/chloroform and treated with either water or 0.2 M hydrochloric acid, each at room temperature or 50°C for two hours.…”

Section: Scheme 2 Synthesis Of Dppa-and Dopo-based Bisphosphorylimides Via Staudinger Reactionmentioning

confidence: 99%

“…These results are consistent with previous studies conducted with N-phosphorylated iminophosphoranes as other Staudinger reaction products which are also stable against hydrolysis. 18,38 The corresponding spectra are shown below. Thermal properties.…”

Section: Scheme 2 Synthesis Of Dppa-and Dopo-based Bisphosphorylimides Via Staudinger Reactionmentioning

confidence: 99%

“…Synthesis is following the procedure according to literature. 38 Triethylammonium bis(6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)amide. DOPO (107.58 g, 497.65 mmol) and triethylamine (50.36 g, 497.65 mmol) were dissolved under argon atmosphere in a three-necked round-bottom flask fitted with a condenser, KPG stirrer and septum in dry CH 3 CN.…”

Section: -Azidodibenzo[ce][12]oxaphosphinin-6-oxide (Dopo-n3mentioning

confidence: 99%

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Synthesis of novel bisphosphorylimides based on Staudinger reaction

Döring¹,

Weber²,

Weinert³

et al. 2020

Arkivoc

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A series of bisphosphorylimides based on the reaction sequence of Atherton-Todd and Staudinger reaction were synthesized. These bisphosphorylimides containing phosphorus in different chemical environments, while the reaction sequence is using mild conditions and moreover can be synthesized in an one-pot procedure. The molecular structures were revealed by nuclear magnetic resonance spectroscopy and x-ray crystallography. The stability of the bisphosphorylimides against hydrolysis and thermal influences was tested which allows an initial estimation about the usage as flame retardant.

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Section: Discussionmentioning

confidence: 79%

Section: Scheme 2 Synthesis Of Dppa-and Dopo-based Bisphosphorylimides Via Staudinger Reactionmentioning

confidence: 99%

Section: Scheme 2 Synthesis Of Dppa-and Dopo-based Bisphosphorylimides Via Staudinger Reactionmentioning

confidence: 99%

Section: -Azidodibenzo[ce][12]oxaphosphinin-6-oxide (Dopo-n3mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of novel bisphosphorylimides based on Staudinger reaction

Döring¹,

Weber²,

Weinert³

et al. 2020

Arkivoc

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N‐phosphorylated Iminophosphoranes based on 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide and their flame‐retardant behavior in epoxy resins

Weinert

Döring

2020

J of Applied Polymer Sci

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Two novel N-phosphorylated iminophosphoranes based on 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) were evaluated as flame retardant (FR) additives. They were incorporated in two different epoxy resin systems (EP) based on diglycidyl ether of bisphenol A (DGEBA) and a novolac glycidyl ether (DEN438) both cured with dicyandiamide/fenuron (D/F). Decomposition temperatures and char yields of the cured EP were evaluated and compared to the corresponding neat EP as well as to structurally related compounds. The flame-retardant properties were investigated using the UL-94 V test and further verified with cone calorimetry. The N-phosphorylated iminophosphoranes with DOPO moieties exhibit distinctive flame-retardant effects in DGEBA/D/F and DEN438/D/F, depending on the chemical environment around the second phosphorus atom, even with low FR content. If the iminophosphorane is triphenyl phosphite based the mode of action is assigned to act mainly in the condensed phase hence being advantageous in DGEBA/ D/F compared to the triphenylphosphine-based iminophosphorane, which in turn is more active in the gas phase resulting in superiority in DEN438/D/F.

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