(Vinyloxy)fluorocyclotriphosphazenes

Abstract

The reaction of the lithium enolate of acetaldehyde, LiOCHCH 2, with hexafluorocyclotriphosphazene, N 3P 3F 6, lead to the series of (vinyloxy)fluorocyclotriphosphazene, N 3P 3F 6−n(OCHCH 2) n (n = 2–5). The 1H NMR data show that throughout the entire series, the substituent is bound through the oxygen end of the ambidentate enolate. The reaction shows a reluctance to go past the trisubstituted stage and the fluorine atom in N 3P 3F(OCHCH 2) 5 can not be removed even under forcing conditions. Evidence from the 1H, 19F and 31P NMR spectra shows that a non-geminal pathway is exclusively followed. Differences in the reaction patterns with enolate anions followed by N 3P 3F 6 and N 3P 3Cl 6 are discussed.