Tsutomu Nitta, Y. Okamoto, H. Sakurai
Oct 20, 1969
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Journal
Journal of Japan Oil Chemists Society
Abstract
Diethyl octenylphosphonate was prepared from oct-1-ene, by the three methods ; (1) free radical addition of PCl3, initiated with peroxide, (2) chlorophosphonation by the system of oct-1-ene-PCl3-O2 (3) Arbuzov reaction of triethylphosphite and octenyl bromide, prepared by treating oct-1-ene with N-bromo-succinic imide. The structure of these products were assigned by the spectra of IR and NMR and other analytical methods. By the method (1), diethyl oct-1-enyl-1-phosphonate was obtained in 13% yield ; by the method (2), the mixture of three types of diethyl α, β-unsaturated octenylphosphonate and diethyl octenyl-phosphonate, which was yielded by the introduction of phosphono group into the saturated part of the olefin, was obtained in 11% yield ; and by the method (3), diethyl oct-2-enylphosphonate was obtained in 70% yield.