Determination of Ring Size in Cyclopolymers from Divinyl Phosphonates

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Abstract
Divinyl phenylphosphonate and divinyl methylphosphonate have been synthesized using modifications of the method of Gefter and Kabachnik. In contrast to the results reported by these authors, it has been possible to obtain soluble, fusible, linear polymers (cyclopolymers) from both monomers by polymerization in dilute solution. By 3 1P NMR spectroscopy it is possible to distinguish and quantitatively determine phosphorus atoms in five- and six-membered ring environments. Using a series of phosphonates as model compounds, this technique has shown that poly(divinyl phenylphosphonate) contains both five- and six-membered ring repeating units in amounts which depend upon the method of polymerization, whereas poly (divinyl methylphosphonate) produced under a variety of conditions contains only six-membered rings. This work has established that 3 1P NMR can be used to determine the ring size in cyclopolymers from divinyl phosphonates by direct analysis of the polymers.