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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 7, 1977 - Issue 8
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Original Articles

A New Synthesis of Indenones

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Pages 553-557 | Received 23 Aug 1977, Published online: 01 Apr 2009

References

  • Yields might be enhanced by the presence of nitrobenzene See the second entry in the Table.
  • Martens , H. and Hoornaert , G. 1972 . Syn. Commun. , 2 : 147
  • Brennan , J. , Cadogan , J. I. G. , Cook , J. and Sharp , J. T. 1975 . J. Chem. Soc. Perkin I , : 1060 In contrast B. D. Baigrie; have reported the synthesis of tetramethylnaphthalene-1, 2, 3,-4-tetracarboxylate from phenyl radical and dimethylacetylene dicarboxylate.
  • The low yields of indenones may possibly be due to trapping of the intermediate radicals by the product. 5
  • Bell , E. A. , Cadogan , J. I. G. , Milburn , P. W. , Murray , C. D. , Paton , R. M. and Sharp , J. T. 1975 . J. Chem. Soc. Chem. Commun. , : 631
  • Since the initial product of coupling may undergo 1, 5-sigmatropic shifts of hydrogen, we are reluctant to postulate an exact structure at this time.
  • White needles, mp 181–183[ddot]. Calcd for C28H20O2: C, 86.57; H, 5.19. Found: C, 86.51; H, 5.30. Molecular weight calculated: 388.1462; found: 388.1460.
  • Molecular weight calculated for C21H16O2: 300.1150; found: 300.1150; infrared 3450 (OH) and 1710 cm-1 (C=0); mp 126–128[ddot], lit9 mp 129–130[ddot].
  • Moureu , C. , Dufraisse , C. and Badoche , M. 1928 . Bull. Soc. Chim. Fr. , 43 : 1386
  • White crystals, mp 143–144[ddot] to a red oil, lit8 mp 141[ddot] to a red oil. Molecular weight calculated for C21H14O2: 298.0991; found: 298.0994.
  • Weitz , E. A. and Scheffer , A. 1921 . Chem. Ber. , 54 : 2341

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