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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 4
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Original Articles

An Improved Synthesis of Hexamethylphenalene

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Pages 401-410 | Published online: 05 Dec 2006

References

  • Ried , D. H. 1965 . Quart. Rev. Chem. Soc. , 19 : 274 For general reviews on phenalene see:
  • Murata , I. 1973 . Topics in Nonbenzenoid Aromatic Chemistry , Edited by: Nozoe , T. , Breslow , R. , Hafner , K. , Ito , S. and Murata , I. Vol. 1 , 159 Wiely Inc. .
  • Haddon , R. C. 1975 . Nature , 256 : 394 For research on the possible use of phenalene as an organic metal see:
  • Haddon , R. C. 1975 . Aust. J. Chem. , 28 : 2343
  • Haddon , R. C. , Wudl , F. , Kaplan , M. L. , Marshall , J. H. , Cais , R. E. and Bramwell , F. B. 1978 . J. Am. Chem. Soc. , 100 : 7629
  • Sato , T. and Yokote , M. 1980 . Senryo to Yakuhin , 25 : 138 For reviews on the biological and dye use of the phenalenyl system see:
  • Cooke , R. G. and Edwards , J. M. 1981 . Prog. Chem. Org. Nat. Prod. , 40 : 153
  • Sato , T. and Yokote , M. 1983 . Senryo to Yakuhin , 28 : 100
  • Pettit , R. 1956 . Chem. Ind. (London) , : 1306 la
  • Boekelheide , V. H. and Larrabee , C. E. 1962 . J. Am. Chem. Soc. , 72 : 1245 Ried, D. H. Chem. Ind. (London), 1956, 1504. Sogo, P. B.; Nakazaki, M.; Calvin, M. J. Chem. Phys., 1957, 26, 1343. Pettit, R. J. Am. Chem. Soc., 1960, 82, 1972. Bennett, J. E. Proc. Chem. Soc., 1961, 144. Stehling, F. C.; Bartz, K. W. J. Chem. Phys., 1961, 34, 1076.1c:
  • Reid , D. H. 1956 . Chem. Ind. (London) , : 1504
  • Pettit , R. 1960 . J. Am. Chem. Soc , 82 : 1972
  • Woell , J. B. and Boudjouk , P. J. 1979 . Organomet. Chem. , 172 : C43 Lin, S.; Boudjouk, P. J. Organomet. Chem., 1980, 187, C11. Boudjouk, P.; Kiely, J. S.; Sooriyakumaran, R. J. Organomet. Chem., 1981, 221, 33. Work on n3 complexes of phenalene have also been done by another group: Nakasuji, K.; Yamaguchi, M.; Murata, I.; Talsumi, K.; Nakamura, A. Organomet., 1984, 3, 1257
  • Boudjouk , P. and Johnson , P. D. J. 1978 . Org. Chem. , 43 : 3979 We have published an improved synthesis of phenalene:
  • Bonthrone , W. and Reid , D. H. 1959 . J. Chem. Soc. , : 2773 1,4,7-trimethylphenalenylium perchlorate, for example, is air stable and can be recrystallized from boiling acetic acid:, Reid, D. H.; Sutherland, R. G., J. Chem. Soc., 1963, 3295
  • Reid , D. H. 1958 . Tetrahedron , 3 : 339 Alkyl substituents also increased the stability of phenalenyl radicals towards dimerization, and slows down the secondary reaction of the dimer to form peropyrene:, Gerson, F. Helv. Chim. Acta, 1966, 49, 1463. Gerson, F.; Heilbronner, E.; Reddoch, H. A.; Paskovic, D. H.; Das, N. C. Helv. Chim. Acta, 1967, 50, 813
  • Canonne , P. 1967 . Tetrahedron Lett. , : 1757
  • Canonne , P. and Leitch , L. C. 1967 . Can. J. Chem. , 45 : 1761 For related procedures see:
  • Canonne , P. , Holm , P. and Leitch , L. C. 1967 . Can. J. Chem. , 45 : 2151
  • Barabas , A. and Balaban , A. T. 1971 . Tetrahedron , 27 : 5495 For a study of the reaction of 1,3-pentanediones with Grignard reagents see:
  • West , R. and Riley , R. J. 1958 . Inorg. Nucl. Chem. , : 295
  • Takamura , K. , Shioga , A. , Yamamoto , T. , Takama , S. and Natta , Y. 1965 . Chem. Pharm. Bull. , 13 : 211 CA, 1965, 62, 14538h
  • While the reaction works without the use of sonication the yield varies considerately depending on the quality of stirring. Using sonication the yield is consistently in the 70–75% range for isolated product
  • Pouchert , C. J. and Campbell , J. R. 1974 . The Aldrich Library of NMR Spectra , Milwaukee, Wisconsin : Aldrich Chemical Company, Inc. .

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