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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 2
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Original Articles

A Convenient Synthesis of Triquinacene

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Pages 161-164 | Received 27 Feb 1973, Published online: 06 Dec 2006

References

  • 1970–1972 . Holder of an NRCC Studentship (Canada)
  • Kingston : Department of Chemistry, University of Rhode-Island . R. I. 02881
  • Sloan Fellow , A. P. 1970–1972 . To whom inquiries should be addressed
  • Russo , R. , Lambert , Y. and Deslongchamps , P. 1971 . Can. J. Chem. , 49 : 531
  • Matsui , T. 1967 . Tetrahedron Letters , : 3761
  • All new compounds reported in this communication gave satisfactory elemental analysis and spectroscopic data. Elemental analysis was not attempted for compounds 3 and 4
  • Bowden , K. , Heilbron , I. M. , Jones , E. R. H. and Weedon , B. C. L. 1946 . J. Chem. Soc. , : 39
  • The trans, diol 15 being unsymmetrical shows a pair of doublets at 5.63 δ (1H) and 5.42 δ (1H) (J = 6 Hz) for the olefinic protons in its n.m.r. spectrum
  • The cis, diol 16 being symmetrical shows a singlet at 5.77 δ (2H) for the olefinic protons in its n.m.r. spectrum
  • Diol 16 gave the cyclic carbonate 17 (m.p. 130–140°, COCl2/pyridine, benzene). This result shows that the cis, diol obtained has the configuration since molecular models indicate that the exo cis, diol structure cannot form a cyclic carbonate
  • Pasner , G. H. , Johnson , R. J. and Whalen , M. J. 1972 . Chem. Comm. , : 281
  • Woodward , R. B. , Fukunaga , T. and Kelly , R. C. 1964 . J. Amer. Chem. Soc. , 86 : 3162
  • Eaton , P. E. and Mueller , R. H. 1972 . J. Amer. Chem. Soc. , 94 : 1014

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