Advertisement

Hydrocarbons Consisting of Six-membered Rings in which Two Carbon Atoms Are Linked with Two Hydrogen Atoms

Abstract

The reaction of o-tolyl magnesium bromide with phthalic anhydride gives di-o-tolylphthalide.1 However, the main product is di-o-tolylbenzene.2 Reduction of the phthalide with sodium amalgam and alkali gives the acid (II), which is oxidized to the tricarboxylic acid (III). Cyclization with sulphuric acid yields the triketone (IV). However this is strongly acidic and must be formulated as 12-hydroxytriangulene4,8-quinone (IVα).

Keywords

Sulphuric Acid Dicarboxylic Acid Acetic Anhydride Colourless Needle Concentrate Sulphuric Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Weisz, R. and Korczyn, J., Mh. Chem. 45, 207 (1924).Google Scholar
  2. 2.
    Clar, E. and Stewart, D. G., J. chem. Soc. 3215 (1951).Google Scholar
  3. 3.
    Clar, E. and Stewart, D. G., J. Amer. chem. Soc. ‘75, 2667 (1953); Amer. Patent 2841597 (1958).Google Scholar
  4. 4.
    Clar, E. and Stewart, D. G., J. Amer. chem. Soc. 75, 2667 (1953); 76, 3505 (1954).Google Scholar
  5. 5.
    Clar, E. and Stewart, D. G., J. Amer. chem. Soc. 76, 3504 (1954).CrossRefGoogle Scholar
  6. 6.
    Clar, E. and Stewart, D. G., J. Amer. them. Soc. ‘75, 2667 (1953).Google Scholar
  7. 7.
    Weisz, R. and Müller, Fr., Mh. Chem. 65, 481 (1934).Google Scholar
  8. 8.
    Weisz, R. and Müller, Fr., Mh. Chem. 59, 128 (1932); Weisz, R., Spitzer, A. and Melzer, J. L., Mh. Chem. 47, 307 (1926).Google Scholar
  9. 1.
    Clar, E., Kemp, W. and Stewart, D. G., Tetrahedron 3, 325 (1958); Gupte, S. D., Nabar, D. P. and Sunthankar, S. V., J. Sci. Ind. Research (India) 19b, 411 (1960).Google Scholar
  10. 1.
    Vollmann, H., Liebigs Ann. 669, 22 (1963).CrossRefGoogle Scholar
  11. 2.
    Clar, E., Macpherson, I. A. and Schulz-Kiesow, H., Liebigs Ann. 669, 44 (1963).CrossRefGoogle Scholar
  12. 1.
    Clar, E., Ber. dtsch. chem. Ges. 73, 409 (1940).CrossRefGoogle Scholar
  13. 2.
    Clar, E., Kemp, W. and Stewart, D. G., Tetrahedron 3, 325 (1958).CrossRefGoogle Scholar
  14. 3.
    Clar, E. and Macpherson, I. A., Tetrahedron 18, 1411 (1962).CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1964

Authors and Affiliations

  • E. Clar
    • 1
  1. 1.University of GlasgowScotland

Personalised recommendations