Accéder directement au contenu Accéder directement à la navigation
Article dans une revue

Synthesis of ω-phosphonated poly(ethylene oxide)s through the combination of kabachnik-fields reaction and “click” chemistry

Abstract : The synthesis of newx-phosphonic acid-terminatedpoly(ethylene oxide) (PEOs) monomethyl ethers was investi-gated by the combination of Atherton–Todd or Kabachnik–Fields reactions and the ‘‘click’’ copper-catalyzed 1,3-dipolarcycloaddition of azides and terminal alkynes. The Atherton–Todd route fails to give the corresponding phosphonic acid-ter-minated PEOs due to competitive cleavage of the PANbondduring the dealkylation step. In contrast, the Kabachnik–Fieldsroute leads with very good yields tox-phosphonic acid-PEOthrough ‘‘click’’ reaction of azido-PEO onto dimethyl aminopro-pargyl phosphonate prepared by Kabachnik–Fields reactionbetween propargylbenzylimine and dimethyl phosphonate,followed by acidic hydrolysis. The reported methodology, pre-cluding the use of anionic polymerization of ethylene oxide,leads to novel well-defined phosphonic acid-terminated PEOsfrom commercially available products in good yields. Moreover,such a strategy can be adapted to anchor phosphonic acid func-tionality onto a wide range of polymers.
Type de document :
Article dans une revue
Liste complète des métadonnées

https://hal-univ-lemans.archives-ouvertes.fr/hal-01905423
Contributeur : Laurent Fontaine Connectez-vous pour contacter le contributeur
Soumis le : jeudi 25 octobre 2018 - 17:27:56
Dernière modification le : dimanche 26 juin 2022 - 02:01:28

Lien texte intégral

Identifiants

Collections

Citation

Thi Thanh Thuy N'Guyen, Karima Oussadi, V. Montembault, Laurent Fontaine. Synthesis of ω-phosphonated poly(ethylene oxide)s through the combination of kabachnik-fields reaction and “click” chemistry. Journal of Polymer Science Part A: Polymer Chemistry, Wiley, 2013, 51 (2), pp.415 - 423. ⟨10.1002/pola.26399⟩. ⟨hal-01905423⟩

Partager

Métriques

Consultations de la notice

33