This article describes the synthesis of cyclic polyphosphoester (PPE) by the ring-closing metathesis (RCM) of different difunctional linear PPEs. Linear PPE precursors were prepared through a selective head-to-tail acyclic diene metathesis polymerization of phenyl dienephosphate monomer using 2-hydroxyethyl acrylate as a selective chain terminator, followed by the transformation of the terminal acrylate functional group into a hydroxyl group utilizing a thiol-Michael addition click reaction. These products were then reacted with the corresponding acyl chloride containing a vinyl end group. The subsequent end-to-end intramolecular coupling reaction was performed under highly dilute conditions. The successful transformation of the linear PPE precursors to cyclic PPE was confirmed by NMR spectroscopy and gel permeation chromatography. The thermal and flame retardant properties of linear and cyclic PPEs were investigated, and their thermal degradation and flame retardance were evaluated, as these are important features for future applications. (C) 2013 Elsevier Ltd. All rights reserved.