Skip to main content

Photochemical cyclization of aromatic compounds via elimination of hydrogen and/or halogen atoms. Formation of carbocycles

  • Chapter
Preparative Organic Photochemistry

Abstract

According to Schmidlin and Garcia-Banus [1] solutions of triphenylmethyl in benzene are not apparently changed after three months. However, in diffuse daylight complete decolorization of the solution occurs with formation of triphenylmethane and 9,9’-diphenyl-9,9’-binuorene (1).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. Schmidlin and A. Garcia-Banus: Ber. dtsch. chem. Ges. 45, 1344 (1912).

    Article  CAS  Google Scholar 

  2. S. T. BowDEN and W. J. Jones: J. Chem. Soc. 1928, 1149.

    Google Scholar 

  3. F. B. Mallory, C. S. Wood, J. T. Gordon, L. C. Lindquist and M. L. Savitz: J. Amer. chem. Soc. 84, 4361 (1962).

    Article  CAS  Google Scholar 

  4. F. B. Mallory, C. S. Wood and J. T. Gordon: J. Amer. chem. Soc. 86, 3094 (1964).

    Article  CAS  Google Scholar 

  5. F. B. Mallory, J. T. Gordon and C. S. Wood: J. Amer. chem. Soc. 85, 828 (1963).

    Article  CAS  Google Scholar 

  6. C. S. Wood and F. B. Mallory: J. Org. Chem. 29, 3373 (1964).

    Article  CAS  Google Scholar 

  7. W. M. Moore, D. D. Morgan and F. R. Stermitz: J. Amer. chem. Soc. 85, 829 (1963).

    Article  CAS  Google Scholar 

  8. P. Hugelshofer, J. Kalvoda and K. Schaffner: Helv. chim. acta 43, 1322 (1960).

    Article  CAS  Google Scholar 

  9. M. V. Sargent and C. J. Timmons: J. Chem. Soc. 1964, 5544.

    Google Scholar 

  10. K. A. Muszkat, D. Gegiou and E. Fischer: Chem. Comm. 1965, 447.

    Google Scholar 

  11. S. M. Kupchan and H. C. Wormser: Tetrahedron Letters 1965, 359.

    Google Scholar 

  12. H. Stobbe: Ber. dtsch. chem. Ges. 40, 3372 (1907).

    Article  CAS  Google Scholar 

  13. F. G. Baddar, L. S. El-Assal and M. Gindy: J. Chem. Soc. 1948, 1270.

    Google Scholar 

  14. N. Campbell, P. S. Davison and H. G. Heller: J. Chem. Soc. 1963, 993.

    Google Scholar 

  15. W. A. Henderson Jr. and E. F. Ullman: J. Amer. chem. Soc. 87, 5424 (1965).

    Article  CAS  Google Scholar 

  16. H. Meyer, R. Bondy and A. Eckert: Monatsh. Chem. 33, 1447 (1912).

    Article  Google Scholar 

  17. G. F. Attree and A. G. Perkin: J. Chem. Soc. 1931, 144.

    Google Scholar 

  18. H. Brockmann and R. Mühlmann: Chem. Ber. 82, 348 (1949).

    Article  CAS  Google Scholar 

  19. H. Brockmann in: Fortschr. Chem. org. Naturstoffe, ed. by L. Zechmeister, Vol. 14, 141–185. Wien: Springer 1957.

    Google Scholar 

  20. A. Schönberg and K. Junghans: Chem. Ber. 98, 2539 (1965).

    Article  Google Scholar 

  21. E. Clar and W. Müller: Ber. dtsch. chem. Ges. 63, 869 (1930).

    Article  Google Scholar 

  22. A. Schönberg, A. F. A. Ismail and W. Asker: J. Chem. Soc. 1946, 442.

    Google Scholar 

  23. A. F. A. Ismail and Z. M. El-Shafei: J. Chem. Soc. 1957, 3393.

    Google Scholar 

  24. A. Eckert: Ber. dtsch. chem. Ges. 58, 322 (1925).

    Article  Google Scholar 

  25. A. Eckert and R. Tomaschek: Monatsh. Chem. 39, 839 (1918).

    Article  CAS  Google Scholar 

  26. W. Dilthey and F. Quint: Ber. dtsch. chem. Ges. 69, 1575 (1936).

    Article  Google Scholar 

  27. IG Farbenindustrie. Swiss pat. 176 926 of 30. 4.1934; Chem. Zentr. 1936 I, 648.

    Google Scholar 

  28. IG Farbenindustrie. French pat. 772 781 of 2. 5. 1934; Chem. Zentr. 1936 I, 648.

    Google Scholar 

  29. R. Huisgen: Liebigs Ann. Chem. 564, 16 (1949).

    Article  CAS  Google Scholar 

  30. W. Carruthers and H. N. M. Stewart: J. Chem. Soc. 1965, 6221.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1968 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Schönberg, A. (1968). Photochemical cyclization of aromatic compounds via elimination of hydrogen and/or halogen atoms. Formation of carbocycles. In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_13

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-87918-0_13

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-87920-3

  • Online ISBN: 978-3-642-87918-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics