Abstract
The reaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane (1) with trimethylsilyl cyanide was found to give, depending on conditions, three organophosphorus compounds: trimethylsilyl methyl(2-cyanocarbonylethyl)phosphinate (2), trimethylsilyl methyl(3-trimethylsiloxy-3,3-dicyanopropyl)phosphinate (3) and trimethylsilyl methyl(3-trimethyl-siloxy-3-cyano-2-propenyl)phosphinate (4), On hydrolysis of3 under mild conditions, methyl(3-hydroxy-3,3 dicarboxypropyl)phosphinic acid (7) was obtained. The latter is readily decarboxylated on heating to give methyl(3-hydroxy-3-carboxy-propyl)phosphinic acid (8). The interaction of2 and4 with water or alcohols gives, correspondingly, methyl[2-carboxy(alkoxycarbonyl) ethyl]phosphinic acids (11–13). Methyl(2-oxamoyiethyl)phosphinic acid (14) was prepared by successive treatment of propenylphosphinate4 with HCl gas and water.
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References
K.Weissermel, H.J.Kleiner. M.Finke, and U.H.Felcht,Angew.Chem., 1981,93, 256.
Pat. 330022 EP,Chem.Abstr.,1990,112, 56281.
Pat. 2614240 FRG,Chem.Abstr.,1978,88, 22423.
Pat. 2614241 FRG, Chem.Abstr.,1978,88, 22422.
G.G.Furin, O.A.Vyazankina, B.A.Gostevsky, and N.S. Vyazankin,Tetrahedron, 1988,44, 2675.
U.Hertenstein, S.Hunig, H.Reichelt, and R.Schaller,Chem.Ber., 1982,115, 261.
D.A.Evans and L.K.Truesdale,Tetrahedron Lett., 1973, 4929.
W.Lidy and W.Sundermeyer,Tetrahedron Lett., 1973, 1449.
W.Lidy and W.Sundermeyer,Chem.Ber., 1973,106, 587.
P.V.Kazakov, I.L.Odinets, M.Yu.Antipin, P.V.Petrovsky, L.V.Kovalenko, Yu.T.Struchkov, and T.A.Mastryukova,Izv. Akad.Nauk SSSR, Ser.Khim., 1990, 2120 [Bull.Acad.Sci. USSR.Div.Chem.Sci., 1990,39, 1931].
H.O.House and V.Kramer,J.Org.Chem., 1963,28, 3362.
E.Taskinen,Tetrahedron, 1978,34, 353.
E.Taskinen,Tetrahedron, 1978,34, 425.
E.I.Lazhko, E.V.Luzikova, G.Yu.Mikhailov, M.A.Kazankova, and Yu.A.Ustynyuk,Zhu.Obshch.Khim., 1988,58, 1247 [J.Gen.Chem. USSR].
S.Hunig and R.Schaller,Angew.Chem.Int.Ed.Engl., 1982,21, 36.
V.K.Khairullin, T.I.Sobchuk, and A.N.Pudovik,Zh. Obshch.Khim., 1967,37, 710 [J.Gen.Chem. USSR].
Pat. 030424 EP,Chem.Abstr., 1985,95, 204142.
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Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 170–177, January, 1993.
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Odinets, I.L., Antonov, E.A., Petrovsky, P.V. et al. Interaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane with trimethylsilyl cyanide. Russ Chem Bull 42, 154–161 (1993). https://doi.org/10.1007/BF00699999
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DOI: https://doi.org/10.1007/BF00699999