REACTION OF DIBROMOALKANES WITH SILYL PHOSPHITES
719
Ethylenebis(phosphonic dichloride) (XXIII).
Phosphorus pentachloride, 20.9 g, was added in
portions to 12 g of diphosphonate XXII at 120 C.
Volatile compounds (chlorotrimethylsilane, PCl3)
were removed, and the residue was washed with ether
to obtain 6.1 g (91%) of compound XXIII, mp 110 C
[26].
6. Ford-Moore, A.H. and Williams, J.H., J. Chem. Soc.,
1947, p. 1465.
7. Schroeder, J.P., Few, L.B., and Peters, V.M., J. Org.
Chem., 1970, vol. 35, no. 9, p. 3181.
8. Gololobov, Yu.G., Voitekunas, Yu.B., Petrovskii, P.V.,
and Polyakova, A.M., Izv. Akad. Nauk SSSR, Ser.
Khim., 1983, no. 9, p. 2170.
Ethylenebis(phenyl phosphonate) (XXV).
A
9. Horner, L. and Lindel, H., Phosphorus, Sulfur Relat.
Elem., 1984, vol. 20, no. 2, p. 161.
solution of 5.28 g of diphosphonate XXIII, 3.76 g of
phenol, and 4.0 g of triethylamine in 80 ml of me-
thylene chloride was refluxed for 1 h. Triethylamine
hydrochloride was separated, the solvent was removed,
and the residue was dried in a vacuum to obtain 3.9 g
(79%) of compound XXV, mp 152 156 C. 31P NMR
spectrum, P, ppm: 21.89. Found P, %: 12.41.
C26H24O6P2. Calculated P, %: 12.55 [27].
10. Hewitt, D.J. and Teese, M.W., Aust. J. Chem., 1984,
vol. 37, no. 1, p. 205.
11. Afaque, S., Ansari, M., Ahmad, F., and Siddiqui, M.,
Indian J. Chem., Sect. B, 1989, vol. 28, no. 4, p. 308.
12. Montoneri, E. and Ricca, G., Phosphorus, Sulfur Relat.
Elem., 1991, vol. 55, nos. 1 4, p. 111.
13. Abel, E.W. and Illingworth, S.M., Organomet. Chem.
Rev. A, 1970, no. 5, p. 143.
Ethylenebis(ethyl N-methylphosphonamidate)
(XXIX). Excess methylamine was passed through a
solution of 5.6 g of chloride XXVII in 30 ml of
methylene chloride. After 4 h methylamine hydro-
chloride was separated, and the solvent was removed
to obtain 4.3 g (79%) of compound XXIX, mp 118
121 C. 31P NMR spectrum, P, ppm: 35.58. Found,
%: N 10.28; P 22.73. C8H16N2O4P2. Calculated, %: N
10.29; P 22.79.
14. Chernyshev, E.A., Bugerenko, E.F., Akat’eva, A.S.,
and Naumov, A.D., Zh. Obshch. Khim., 1975, vol. 45,
no. 1, p. 242.
15. Pudovik, M.A., Medvedeva, M.D., and Pudovik, A.N.,
Zh. Obshch. Khim., 1975, vol. 45, no. 3, p. 700.
16. Lebedev, E.P., Pudovik, A.N., Tsyganov, B.N., Naz-
mutdinov, R.Ya., and Romanov, G.V., Zh. Obshch.
Khim., 1977, vol. 47, no. 4, p. 765.
17. Kurdyumova, N.R., Ragulin, V.V., and Tsvetkov, E.N.,
Zh. Obshch. Khim., 1996, vol. 66, no. 5, p. 769.
18. Sekine, M., Jkimoto, K., Jamada, K., and Hata, T.,
J. Org. Chem., 1981, vol. 46, no. 10, p. 2097.
19. Issleib, K., Mogelin, W., and Balsuweit, A., Z. Anorg.
Allg. Chem., 1985, vol. 530, no. 11, p. 16.
20. Rozhko, L.F., Ragulin, V.V., and Tsvetkov, E.N.,
Zh. Obshch. Khim., 1997, vol. 67, no. 12, p. 1974.
21. Pudovik, M.A., Al’myanova, R.Kh., Kamalov, R.M.,
and Pudovik, A.N., Zh. Obshch. Khim., 1996, vol. 66,
no. 3, p. 364.
22. Kabachnik, M.I. and Rossiiskaya, P.A., Izv. Akad.
Nauk SSSR, Otd. Khim. Nauk, 1946, no. 3, p. 295.
23. Knunyants, I.L., Puzerauskas, A.P., Kil’disheva, O.V.,
and Pervova, E.Ya., Izv. Akad. Nauk SSSR, Ser. Khim.,
1966, no. 6, p. 1115.
ACKNOWLEDGMENTS
The work was financially supported by the Russian
Foundation for Basic Research (project no. 03-03-
33064).
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