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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 18
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Original Articles

Ti(III) Salt Mediated Formation of 1,3-Dioxolanes

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Pages 2281-2287 | Published online: 03 Jan 2007

References

  • Clerici , A. and Porta , O. 1982 . Tetrahedron , 38 : 1293
  • Clerici , A. and Porta , O. 1985 . La Chimicae l'Industria , 67 : 187
  • Clerici , A. and Porta , O. 1982 . J. Org. Chem. , 47 : 2852
  • Clerici , A. and Porta , O. 1983 . J. Org. Chem. , 48 : 1690
  • Clerici , A. , Porta , O. and Zago , P. 1986 . Tetrahedron , 42 : 561
  • Beckett , A. , Osborne , A. D. and Porter , G. 1964 . Trans Faraday Soc. , 60 : 873 Data from the literature suggest that ketyl radical from benzil disproportionates rather than dimerizes due to steric effect:, Other authors report that the dimer is very unstable both thermally and in solution: Bunbury, D.L. and Wang, C.T., Canad. J. Chem., 1968, 46, 1473
  • Flowers , H. M. 1971 . The Chemistry of the Hydroxyl Group Edited by: Patai , S. 1029 London
  • Actually, at 0°C, only the more abundant isomer precipitates directly from the reaction mixture: see Experimental Section
  • Schmitz , E. and Eichhorn , I. 1967 . The Chemistry of the Ether Linkage Edited by: Patai , S. 316 London
  • We have already reported that the unusual nucleophilic substitutions: R-OH + Cl−→ - R-Cl and Ph-C(O)Br + Cl−→ Ph-C(O)Cl are catalized by titanium ion that assists the departure of the hydroxylic oxygen and the bromide ion to which is already bonded or coordinated: (a) See Ref. 2c; (b) Clerici, A. and Porta, O., Tetrahedron Lett., 1987, 28, 1541
  • Korth , H. G. , Sustmann , R. , Merenyi , R. and Viehe , H. G. 1983 . J. Chem. Soc. Perkin Trans II , : 67
  • Maruyama , K. and Katagiri , T. 1986 . J. Am. Chem. Soc. , 108 : 6263
  • Adams , W. R. 1974 . Ger. Offen. , 2 : 357, 866 C.A., 1974, 81, 170273f;
  • Viehe , H. G. , Rosenkranz , H. J. and Rudolph , H. 1972 . Angew. Chem. Int. Edit. , 11 : 974
  • The physical data were obtained as follows: melting points in a Koffler apparatus (uncorrected), IR spectra on a Perkin-elmer E 177, Mass spectra on a Hitachi-Perkin-Elmer RMU 6D at 70 eV, 1H NMR spectra on a Varian EM-390 (90 MHz) with Me4Si as an internal standard. Elemental analysis of the products was satisfactory.

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