Phosphonation of aryloxyphosphazenes

Harry R. Allcock; Michael A. Hofmann; Richard M. Wood

doi:10.1021/ma010258p

Phosphonation of aryloxyphosphazenes

Harry R. Allcock, Michael A. Hofmann, Richard M. Wood

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48 Scopus citations

Abstract

Two methods for the addition of pendent dialkyl phosphonate units onto aryloxyphosphazenes, at both the polymeric and cyclic trimer levels, are described. Sodium organophosphates or halogenated organophosphates were used as the phosphonating agents and were allowed to react with bromomethylene- or lithio-functionalized aryloxyphosphazenes, respectively. Phosphonation of bromomethylene-phenoxy side groups proceeded with ∼100% conversion, while phosphonation via lithiophenoxy intermediates yielded 80-85% conversion. The presence of a direct phosphorus-carbon bond in all products was confirmed by ¹³C NMR. Well-defined, cyclic trimers and polymers were obtained via both methods.

Original language	English (US)
Pages (from-to)	6915-6921
Number of pages	7
Journal	Macromolecules
Volume	34
Issue number	20
DOIs	https://doi.org/10.1021/ma010258p
State	Published - Sep 25 2001

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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abstract = "Two methods for the addition of pendent dialkyl phosphonate units onto aryloxyphosphazenes, at both the polymeric and cyclic trimer levels, are described. Sodium organophosphates or halogenated organophosphates were used as the phosphonating agents and were allowed to react with bromomethylene- or lithio-functionalized aryloxyphosphazenes, respectively. Phosphonation of bromomethylene-phenoxy side groups proceeded with ∼100% conversion, while phosphonation via lithiophenoxy intermediates yielded 80-85% conversion. The presence of a direct phosphorus-carbon bond in all products was confirmed by 13C NMR. Well-defined, cyclic trimers and polymers were obtained via both methods.",

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T1 - Phosphonation of aryloxyphosphazenes

AU - Allcock, Harry R.

AU - Hofmann, Michael A.

AU - Wood, Richard M.

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Y1 - 2001/9/25

N2 - Two methods for the addition of pendent dialkyl phosphonate units onto aryloxyphosphazenes, at both the polymeric and cyclic trimer levels, are described. Sodium organophosphates or halogenated organophosphates were used as the phosphonating agents and were allowed to react with bromomethylene- or lithio-functionalized aryloxyphosphazenes, respectively. Phosphonation of bromomethylene-phenoxy side groups proceeded with ∼100% conversion, while phosphonation via lithiophenoxy intermediates yielded 80-85% conversion. The presence of a direct phosphorus-carbon bond in all products was confirmed by 13C NMR. Well-defined, cyclic trimers and polymers were obtained via both methods.

AB - Two methods for the addition of pendent dialkyl phosphonate units onto aryloxyphosphazenes, at both the polymeric and cyclic trimer levels, are described. Sodium organophosphates or halogenated organophosphates were used as the phosphonating agents and were allowed to react with bromomethylene- or lithio-functionalized aryloxyphosphazenes, respectively. Phosphonation of bromomethylene-phenoxy side groups proceeded with ∼100% conversion, while phosphonation via lithiophenoxy intermediates yielded 80-85% conversion. The presence of a direct phosphorus-carbon bond in all products was confirmed by 13C NMR. Well-defined, cyclic trimers and polymers were obtained via both methods.

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JO - Macromolecules

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Phosphonation of aryloxyphosphazenes

Abstract

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