Abstract
The allyl phosphoester group is shown to be a protecting group for the synthesis of anionic polyphosphodiesters. Our strategy relies on the synthesis of a cyclic phosphate monomer bearing a pendant allyl phosphoester group, its easy purification by fractional distillation, its organocatalyzed ring-opening polymerization by 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) and 1-[3,5-bis(trifluoromethyl)phenyl]-3-cyclohexyl-thiourea (TU). Finally, the deprotection of the allyl phosphoester group is carried out by reaction with sodium benzenethiolate in the absence of any detectable degradation.
Original language | English |
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Pages (from-to) | 2642-2648 |
Journal | Journal of Polymer Science Part A-Polymer Chemistry |
Volume | 53 |
Issue number | 22 |
DOIs | |
Publication status | Published - 15 Nov 2015 |
Keywords
- aliphatic polyphosphodiesters
- biodegradable
- cyclic phosphate
- degradable polymer
- organocatalysis
- polyelectrolytes
- ring-opening polymerization
- water-soluble polymers