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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 5
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Original Articles

The Synthesis of Aporphine Alkaloids. III.1 Steric Effects in the Pschorr Cyclization

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Pages 303-306 | Received 23 Jun 1972, Published online: 05 Dec 2006

References

  • Dalton , D. R. , Miller , S. I. , Dalton , C. K. and Crelling , J. K. 1971 . Tetrahedron Letters , : 575 For paper II in this series see:
  • DeTar , D. F. 1951 . Organic Reactions , Vol. 9 , 409 N. Y. : J. Wiley and Sons, Inc. .
  • Williams , G. H. 1960 . Homolytic Aromatic Substitution , Oxford, , England : Pergamon Press .
  • Cava , M. P. and Dalton , D. R. 1966 . J. Org. Chem. , 31 : 1281 See e. g. and references therein
  • Satisfactory elemental, mass spectral and pmr analyses were obtained for all reported compounds
  • Reactions were run as follows: 1 eq. of base in acetic acid sulfuric acid (12:1) was treated with 2 eq. of NaNO2 in the minimum amount of water. The reaction mixture was held at 10° for ca. 30 min and the excess nitrous destroyed with sulfamic acid. After addition of the catalyst (10 eq.) and acetone (twice the volume of the total solution) and refluxing for 30 min the solvent was removed at reduced pressure, the residue basified with aqueous ammonia and the resulting solution continuously extracted with ether
  • The yields reported are yields of isolated material and an average of at least three independent determinations
  • Copper was freshly prepared from CuSO4 and purified zinc dust in distilled water and washed with distilled water and reagent grade acetone prior to use
  • Dalton , D. R. , Ramey , K. C. , Gisler , H. J. Jr. , Lendvay , L. J. and Abraham , A. 1969 . J. Amer. Chem. Soc. , 91 : 6367

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