Vinyloxycyclophosphazenes

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Abstract
Numerous vinyloxyphosphazenes, NyPyX2y-n (OCH=CH2)n (y=3,4; X=Cl, F; n=1–2y) are available via reactions of the enolate anion of acetaldehyde with halocyclophosphazenes. We have now shown that the cis stereoisomer is the predominant species formed in many of these reactions. An electrostatic model has been proposed to account for this observation. The reaction of vinyloxyphosphazenes with other nucleophiles has been examined. Mixed vinyloxy/trifluoroethoxy derivative have been prepared. Studies involving 13C nmr spectroscopy and vinyl addition polymerization show that the electron distribution in the vinyl group is strongly influenced by the electron donor ability of the geminal phosphazene substituent. The methacryloyl ethylenedioxy derivative, N3P3Cl5OCH2CH2OC(O)C(CH3)=CH2, was prepared. This material undergoes a slow phosphazene-phosphazane rearrangement.