40 Prishchenko et al.
REFERENCES
Phosphinate 13 Was Prepared Similarly
[1] Kolodiazhnyi, O.I. Usp Khim 2006, 75, 254–282 (in
Russian).
[2] Ebetino, F.H. Phosphorus Sulfur Silicon Relat Elem
1999, 144–146, 9–12.
[3] Matkovskaya, T.A., Popov, K.I.; Yurieva, E.A.
Bisphosphonates. Properties, Structure, and Medical
Applications; Khimiya: Moscow, 2001 (in Russian).
[4] Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Milaeva, E.R. Heteroat Chem 2008,
19, 490–494.
[5] Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Milaeva, E.R. Heteroat Chem 2008,
19, 562–568.
O,O,O,O-Tetraethyl (1,3-pentadien-1-yl)trimethylsi-
loxymethylenebisphosphonate (14). A solution of
sorbinoyl chloride, 6 g, in 15 mL of methylene
chloride was added with stirring and cooling to
10◦C to a solution of 21 g of diethyl trimethylsilyl
phosphite in 20 mL of methylene chloride. The
mixture was stirred for 0.5 h and heated to reflux;
then the solvent was distilled off and the residue
was kept in a vacuum (0.5 mm Hg) for 1 h at 30◦C.
Bisphosphonate 14 was obtained as a thick oil, a
yield of 19.5 g.
[6] Tyurin, V.Yu.; Gracheva, Yu.A.; Milaeva, E.R.;
Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Maryashkin, A.V.; Bubnov, M.P.;
Kozhanov, K.A.; Cherkasov, V.K. Russ Chem Bull
2007, 744–750.
[7] Berberova, N.T.; Osipova, V.P.; Koljada, M.N.;
Antonova, N.A.; Zefirov, N.S.; Milaeva, E.R.;
Filimonova, S.I., Gracheva, Yu.A.; Prishchenko, A.A.;
Livantsov, M.V.; Livantsova, L.I.; Novikova, O.P.
Patent RU 2405032 C 1, Int. Cl. C11B 5/00. Russian
Patent Bull 2010, 33 (in Russian).
[8] Hilgetag, G.; Martini, A. Weygand-Hilgetag.
Organish-Chemische Experimentierkunst; Khimia:
Moscow, 1968 (in Russian).
[9] Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Petrosyan, V.S. Heteroat Chem
2008, 19, 345–351.
Compounds 15–29 Were Prepared Similarly
Sodium
(1-hydroxy-2,4-hexadien-1-yl)phosphonite
(30). A solution of 15.2 g of phosphonite 8 in 20 mL
of diethyl ether was added with stirring and cooled
at 10◦C to a solution of 2.16 g of sodium methylate
in 30 mL of methanol. The resulting mixture was
heated to a boil, the solvent was removed in a
vacuum, and the residue was kept in a vacuum
(1 mm Hg) for 1 h to obtain 7.1 g of salt 30 as yellow
hygroscopic crystals.
Salt 31 Was Obtained Similarly
[10] Wozniak, L.; Chojnowski, J. Tetrahedron 1989, 45,
2465–2524.
[11] Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Petrosyan, V.S. Heteroat Chem
2008, 19, 352–359.
[12] Sekine, M.; Hata, T. Chem Commun 1978,
285.
[13] Prishchenko, A.A.; Livantsov, M.V.; Novikova, O.P.;
Livantsova, L.I.; Petrosyan, V.S. Heteroat Chem
2008, 19, 418–428.
Bis(1-hydroxy-2,4-hexadien-1-yl)phosphinic
acid
(32). Phospinate 10, 18 g, was added with stirring
to 60 mL of methanol cooled to 10◦C. The mixture
was heated to boiling and then was distilled off; the
residue was kept in a vacuum (1 mm Hg) for 1 h to
obtain 9.5 g of acid 32. Acids 33–45 were prepared
similarly.
Heteroatom Chemistry DOI 10.1002/hc