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A Rapid, Convenient, Solventless Green Approach for the Synthesis of a-Hydroxyphosphonates by Grinding
Corresponding Author(s) : Peng-Wei Zhang
Asian Journal of Chemistry,
Vol. 26 No. 4 (2014): Vol 26 Issue 4
Abstract
An efficient and convenient approach to the condensation reaction of aromatic aldehydes and diethyl phosphite using Na2CO3 as catalyst with grinding at room temperature (without any solvent) is described. This method provides several advantages such as neutral condition, simple work-up procedure, high yields and reduced environmental impact.
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- J.G. Dingwall, U.K. Patent 1542938(1979).
- R. Engel, Chem. Rev., 77, 349 (1977); doi:10.1021/cr60307a003.
- B. Iorga, F. Eymery and P. Savignac, Tetrahedron, 55, 2671 (1999); doi:10.1016/S0040-4020(99)00037-X.
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- R.U. Pokalwar, R.V. Hangarge, P.V. Maske and M.S. Shingare, ARKIVOC, 2006, 196 (2006); doi:10.3998/ark.5550190.0007.b20.
- Y. Ishiguri, E.P. Patent, 82-301905(1982).
- D.V. Patel, K. Rielly-Gauvin and D.E. Ryono, Tetrahedron Lett., 31, 5587 (1990); doi:10.1016/S0040-4039(00)97903-6.
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- A.A. Smaardijk, S. Noorda, F. van Bolhuis and H. Wynberg, Tetrahedron Lett., 26, 493 (1985); doi:10.1016/S0040-4039(00)61920-2.
- V.J. Blazis, K.J. Koeller and C.D. Spilling, J. Org. Chem., 60, 931 (1995); doi:10.1021/jo00109a025.
- T. Yokomatsu, T. Yamagishi and S. Shibuya, J. Chem. Soc. Perkin Trans. I, 1527 (1997); doi:10.1039/a608161d.
- N. Azizi and M.R. Saidi, Phosphorus Sulfur Silicon Rel. Elem., 178, 1255 (2003); doi:10.1080/10426500307904.
- (a) K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.; (b) Z.J. Ren, W.G. Cao and W.Q. Tong, Synth. Commun., 32, 3475 (2002); doi:10.1081/SCC-120014780.; (c) F. Toda, K. Tanaka and K. Hamai, J. Chem. Soc. Perkin Trans., 3207 (1990); doi:10.1039/p19900003207.; (d) F. Toda, T. Suzuki and S. Higa, J. Chem. Soc. Perkin Trans. I, 3251(1998); (e) K. Tanaka, S. Kishigami and F. Toda, J. Org. Chem., 56, 4333 (1991); doi:10.1021/jo00013a055.; (f) F. Toda, K. Kiyoshige and M. Yagi, Angew. Chem. Int. Ed. Engl., 28, 320 (1989); doi:10.1002/anie.198903201.; (g) H. Hagiwara, S. Ohtsubo and M. Kato, Mol. Cryst. Liq. Cryst., 279, 291 (1996).
References
J.G. Dingwall, U.K. Patent 1542938(1979).
R. Engel, Chem. Rev., 77, 349 (1977); doi:10.1021/cr60307a003.
B. Iorga, F. Eymery and P. Savignac, Tetrahedron, 55, 2671 (1999); doi:10.1016/S0040-4020(99)00037-X.
G.A. Olah and A.H. Wu, J. Org. Chem., 56, 902 (1991); doi:10.1021/jo00002a085.
R.U. Pokalwar, R.V. Hangarge, P.V. Maske and M.S. Shingare, ARKIVOC, 2006, 196 (2006); doi:10.3998/ark.5550190.0007.b20.
Y. Ishiguri, E.P. Patent, 82-301905(1982).
D.V. Patel, K. Rielly-Gauvin and D.E. Ryono, Tetrahedron Lett., 31, 5587 (1990); doi:10.1016/S0040-4039(00)97903-6.
A.R. Sardarian and B. Kaboudin, Synth. Commun., 27, 543 (1997); doi:10.1080/00397919708003324.
V. Thottempudi and K.-H. Chung, Bull. Korean Chem. Soc., 29, 1781 (2008); doi:10.5012/bkcs.2008.29.9.1781.
X. Zhou, X. Liu, X. Yang, D. Shang, J. Xin and X. Feng, Angew. Chem. Int. Ed., 120, 398 (2008); doi:10.1002/ange.200704116.
A.A. Smaardijk, S. Noorda, F. van Bolhuis and H. Wynberg, Tetrahedron Lett., 26, 493 (1985); doi:10.1016/S0040-4039(00)61920-2.
V.J. Blazis, K.J. Koeller and C.D. Spilling, J. Org. Chem., 60, 931 (1995); doi:10.1021/jo00109a025.
T. Yokomatsu, T. Yamagishi and S. Shibuya, J. Chem. Soc. Perkin Trans. I, 1527 (1997); doi:10.1039/a608161d.
N. Azizi and M.R. Saidi, Phosphorus Sulfur Silicon Rel. Elem., 178, 1255 (2003); doi:10.1080/10426500307904.
(a) K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.; (b) Z.J. Ren, W.G. Cao and W.Q. Tong, Synth. Commun., 32, 3475 (2002); doi:10.1081/SCC-120014780.; (c) F. Toda, K. Tanaka and K. Hamai, J. Chem. Soc. Perkin Trans., 3207 (1990); doi:10.1039/p19900003207.; (d) F. Toda, T. Suzuki and S. Higa, J. Chem. Soc. Perkin Trans. I, 3251(1998); (e) K. Tanaka, S. Kishigami and F. Toda, J. Org. Chem., 56, 4333 (1991); doi:10.1021/jo00013a055.; (f) F. Toda, K. Kiyoshige and M. Yagi, Angew. Chem. Int. Ed. Engl., 28, 320 (1989); doi:10.1002/anie.198903201.; (g) H. Hagiwara, S. Ohtsubo and M. Kato, Mol. Cryst. Liq. Cryst., 279, 291 (1996).