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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 1
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Original Articles

The Synthesis of Some 2-Substituted Morpholines

Pages 59-73 | Received 07 Aug 1979, Published online: 03 Jan 2007

References

  • 1,138,405; Chem. Abstr., 70 96804 j,(1969) Patent U. K.
  • Patent , U. K. Preparation of (1) and (2) by a six stage synthesis has been described previously:, 1,310,236;Chem. Abstr., 78, 159633 r (1973)
  • Belg. Patent, 828,822;Chem. Abstr., 84, 44089 z(1976)
  • Cottle , D. L. , Jeltsch , A. E. , Stoudt , T. H. and Walter , D. R. 1946 . J. Org. Chem. , 11 : 286 For previous work on the preparation of C-alkyl morpholines from alkyl substitituted diethanolamines, see:
  • Brederick , H. , Gomper , R. and Theilig , G. 1954 . Chem. Ber. , 4 : 537
  • Jpn. Patent, 4494/64;Chem. Abstr., 61, 5661 h (1964)
  • Ger. Patent, 2,520,872;Chem. Abstr., 84, 44088 y (1976)
  • Nef , J. U. 1899 . Ann., 308, 264
  • Noland , W. E. 1955 . Chem. Rev. , 55 : 137
  • The following methods for conversion of the nitromethyl group in (13) and (14) to a carbonyl compound, were tried
  • Johnson , K. and Degering , E. F. 1943 . J. Org. Chem. , 8 : 10 Using sodium hydroxide and sulphuric acid
  • Jacobson , R. M. 1974 . Tetrahedron Lett. , : 3215 Using sodium methoxide and sulphuric acid in methanol.
  • Schechter , H. and Williams , F. T. Jr. 1962 . J. Org. Chem. , 27 : 3699 Using potassium permanganate.
  • McMurray , J. E. and Melton , J. 1971 . J. Am. Chem. Soc. , 93 : 5309 Using titanium trichloride.
  • Keinan , E. and Mazur , Y. 1977 . J. Am. Chem. Soc. , 99 : 3862 Using basic silica gel
  • Ger. Patent, 1,085,153;Chem. Abstr., 55, 17661 h (1961)
  • Schmid , H. and Grob , E. 1949 . Helv. Chim. Acta , 32 : 77

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