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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 1
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Original Articles

A Convenient Synthesis of 5-Oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran Derivatives Catalyzed by KF-Alumina

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Pages 119-126 | Received 09 Oct 2001, Published online: 20 Aug 2006

References

  • Clark , J.H. 1980 . Fluoride ion as a base in organic synthesis . Chem. Rev. , 80 ( 5 ) : 429
  • Ando , T. and Yamawaki , J. 1981 . Multiphase synthesis by fluoride anion . Yuki Gosei Kaga Ku Kyokaishi. , 39 ( 1 ) : 14 Chem. Abstr., 94 (1981), 191060t
  • Yamawaki , J. , Kawate , T. , Ando , T. and Hanafusa , T. 1983 . Potassium fluoride on alumina. An efficient solid base for elimination, addition, and condensation . Bull. Chem. Soc. Jpn. , 56 ( 6 ) : 1885
  • Villemin , D. and Ricard , M. 1984 . Activation of weakly acidic carbon-hydrogen bonds by adsorption on potassium fluoride-alumina . Tetrahedron Lett. , 25 ( 10 ) : 1059
  • Gao , Y. , Shi , D.Q. , Zhou , L.H. and Dai , G.Y. 1996 . Condensation reaction of carbonyl with acid methylene compound catalyzed by potassium fluoride on alumina . Youji Huaxue (Ch) , 16 ( 6 ) : 548 Chem. Abstr. 1997, 126, 171372x
  • Shi , D.Q. , Lu , Z.S. , Wang , S.H. , Tu , S.J. and Dai , G.Y. 1998 . A convenient synthesis of (3-oxo 1,3-diaryl) propylpropane dinitriles catalyzed by KF-alumina . Synth. Commun. , 28 ( 21 ) : 4003
  • X-ray crystallography for 3c: Empirical formula C19H18N2O4, F w  = 338.35, T = 297(2) K, monoclinic, space group C2/c, a = 26.753(5) Å, b = 9.409(2) Å, c = 16.036(2) Å, α = 90°, β = 121.000(10)°, γ = 90°, V = 3460.0(12) Å3, Z = 8, Dc = 1.299 Mg/m3, λ (MoKα) = 0.71073 Å, μ = 0.092 mm−1, F(000) = 1424. 1.78°<θ<25.25°, R = 0.0410, wR = 0.0926. S = 0.905, largest diff. peak and hole: 0.161 and − 0.159 eċÅ−3
  • X-ray crystallography for 3n: Empirical formula C19H20ClNO4, F w  = 361.81, T = 297(2)K, triclinic, space group P-1, a = 8.519(2) Å, b = 10.346(2) Å, c = 11.481(2) Å, α = 108.16(1)°, β = 107.78(2)°, γ =  91.83(2)°, V = 906.5(3) Å3, Z = 2, Dc = 1.326 Mg/m3, λ(MoKα) = 0.71073 Å, μ = 0.234 mm−1, F(000) = 380. 1.98°<θ<25.00°, R = 0.0467, wR = 0.1270. S = 1.050, largest diff. peak and hole: 0.487 and −0.423 e.Å−3

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