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Synthesis and Crystal Structure of Diethyl Tosyloxybenzylphosphonate
Corresponding Author(s) : Du-Lin Kong
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
Diethyl tosyloxybenzylphosphonate was synthesized by the reaction of hydroxybenzylphosphonate with p-toluenesulfonyl chloride characterized by NMR spectroscopy, elemental analyses and X-ray single-crystal diffraction. The possessing parameters: m.f. C18H23O6PS, monoclinic, P2(1)/n, a = 8.1087(9) Å, b = 20.215(2) Å, c = 12.5201(12)Å, a = 90º, b = 98.7380(10)º, g = 90º, V = 2028.5(4) Å3, Z = 4, Mr = 398.39, Dc = 1.305 g/cm3, μ = 0.268 mm-1, F(000) = 840, T = 298(2) K, R1 = 0.0462, wR2 = 0.1076 for 3579 observed reflections with I >2s(I).
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References
M. Horiguchi and M. Kandatsu, Nature, 184, 901 (1959); doi:10.1038/184901b0.
S. Bhagat and A.K. Chakraborti, J. Org. Chem., 72, 1263 (2007); doi:10.1021/jo062140i.
K. Ando and T. Egami, Heteroatom Chem., 22, 358 (2011); doi:10.1002/hc.20689.
M. Hosseini-Sarvari, Tetrahedron, 64, 5459 (2008); doi:10.1016/j.tet.2008.04.016.
M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem., 32, 1652 (1989); doi:10.1021/jm00127a041.
E.W. Logusch, D.M. Walker, J.F. McDonald, G.C. Leo and J.E. Franz, J. Org. Chem., 53, 4069 (1988); doi:10.1021/jo00252a034.
P.P. Giannousis and P.A. Bartlett, J. Med. Chem., 30, 1603 (1987); doi:10.1021/jm00392a014.
L. Maier, Phosphorus Sulfur Silicon, 53, 43 (1990); doi:10.1080/10426509008038012.
E. Alonso, E. Alonso, A. Solís and C. del Pozo, Synlett, 698 (2000); doi:10.1055/s-2000-6615.
N.P. Camp, P.C.D. Hawkins, P.B. Hitchcock and D. Gani, Bioorg. Med. Chem. Lett., 2, 1047 (1992); doi:10.1016/S0960-894X(00)80616-2.
F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem., 29, 29 (1986); doi:10.1021/jm00151a005.
R. Hirschmann, A.B. Smith, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K. Yager, P. Sprengeler and S. Benkovic, J. Sci., 265, 234 (1994); doi:10.1126/science.8023141.
Z.Q. Shang, R.Y. Chen and Y. Hang, Chinese J. Struct. Chem., 25, 1453 (2006).
R.L. Beddoes, L. Dalton, J.A. Joule, O.S. Mills, J.O. Street and C.I.F. Watt, J. Chem. Soc. Perkin Trans. II, 787 (1986); doi:10.1039/p29860000787.
J.G. Rodriguez, F. Temprano, C. Esteban-Calderon, M. Martinez-Ripoll and S. Garcia-Blanco, Tetrahedron, 41, 3813 (1985); doi:10.1016/S0040-4020(01)91402-4.