Synthesis and spectral characteristics of 6-O/S-alkoxyethyl-12H-[1,3,2]dioxaphosphocin-6-oxides/sulfides

From bis(3,5-dichloro-2-hydrxy-phenyl)methane (1), the new [1,3,2] dioxaphosphocins 5, 6 and 7 were synthesized. 1 reacted with POCl3 or PSCl3 to give cyclic compound 2 or 3, which reacted with monoalkyl-1,2-ethandiol to offer 5 or 6. 7 was prepared by the reaction of 1 with P4S10 in the presence of triethylamine, and then reacted with 2-alkoxyl ethyl bromide. The H-1, C-13 and P-31 NMR and MS spectra of the new compounds were evaluated and discussed. The coupling (5)J(PH) (about 0.9 Hz) of P and (CH)-H-1 or (CH)-H-3 was observed in the first time. A solid compound 8 was separated from the crude product 5 and its structure was determined. When 1 and POCl3 reacted at the molar ratio of 3 : 2, 8 was obtained in yield of 70%.