Skip to main content
SpringerLink
Log in

Photohalogenation

  • Chapter
Preparative Organic Photochemistry

Abstract

The effect of light on the reactions of chlorine and bromine with organic compounds is a phenomenon ranking as one of the oldest and most frequently investigated in organic photochemistry. It is noteworthy that one of these well-known reactions, the photochlorination of benzene, has achieved great industrial importance since it was found that one of the stereoisomers from the group of hexachlorocyclohexanes formed is an excellent insecticide (Gammexane).

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

Access this chapter

Log in via an institution
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. G. Sosnovsky: Free Radical Reactions in Preparative Organic Chemistry, pp. 282–413. New York: Macmillan 1964.

    Google Scholar 

  2. J. D. Roberts and P. H. Dirstine: J. Amer. chem. Soc. 67, 1281 (1945).

    Article  CAS  Google Scholar 

  3. H. B. Hass, E. T. McBee and P. Weber: Ind. Eng. Chem. 28, 333 (1936).

    Article  CAS  Google Scholar 

  4. G. A. Russell and H. C. Brown: J. Amer. chem. Soc. 77, 4025 (1955).

    Article  CAS  Google Scholar 

  5. R. N. Haszeldine: J. Chem. Soc. 1952, 2504.

    Google Scholar 

  6. S. A. Faseeh: J. Chem. Soc. 1953, 3708.

    Google Scholar 

  7. R. N. Haszeldine: J. Chem. Soc. 1953, 3565.

    Google Scholar 

  8. R. E. Slade: Chem. and Ind. 1945, 314.

    Google Scholar 

  9. T. van der Linden: Ber. dtsch. chem. Ges. 45, 231 (1912).

    Article  Google Scholar 

  10. L. A. Miller, J. H. Dunn, C. M. Neher and S. N. Hall: USP 2, 622, 105 of 16. 12. 1952.

    Google Scholar 

  11. J. H. Brown: Personal communication to A. Schönberg.

    Google Scholar 

  12. J. T. Rucker: USP 2, 687, 417 of 24. 8. 1954.

    Google Scholar 

  13. G. Wittig and F. Vidal: Chem. Ber. 81, 368 (1948).

    Article  CAS  Google Scholar 

  14. M. Weizmann and S. Patai: J. Amer. chem. Soc. 68, 150 (1946).

    Article  CAS  Google Scholar 

  15. G. Calingaert, M. E. Griffing, E. R. Kerr, A. J. Kolka and H. D. Orloff: J. Amer. chem. Soc. 73, 5224 (1951).

    Article  CAS  Google Scholar 

  16. A. J. Kolka, H. D. Orloff and M. E. Griffing: J. Amer. chem. Soc. 76, 1244 (1954).

    Article  CAS  Google Scholar 

  17. G. G. Ecke, L. R. Buzbee and A. J. Kolka: J. Amer. chem. Soc. 78, 79 (1956).

    Article  CAS  Google Scholar 

  18. C. S. Rondestvedt jr., R. L. Grimsley and C. D. ver Nooy: J. Org. Chem. 21, 206 (1956).

    Article  CAS  Google Scholar 

  19. B. Miller and C. Walling: J. Amer. chem. Soc. 79, 4187 (1957).

    Article  CAS  Google Scholar 

  20. C. E. Griffin and R. N. Haszeldine: J. Chem. Soc. 1960, 1398.

    Google Scholar 

  21. M. Ballester, C. Molinet and J. Castañer: J. Amer. chem. Soc. 82, 4254 (1960).

    Article  CAS  Google Scholar 

  22. O. Bastiansen and O. Hassel: Acta Chem. Scand. 1, 489 (1947).

    Article  CAS  Google Scholar 

  23. D. E. Applequist, G. F. Fanta and B. W. Henrikson: J. Amer. chem. Soc. 82, 2368 (1960).

    Article  CAS  Google Scholar 

  24. J. D. Roberts and R. H. Mazur: J. Amer. chem. Soc. 73, 2509 (1951).

    Article  CAS  Google Scholar 

  25. G. A. Russell: J. Amer. chem. Soc. 80, 4987 (1958).

    Article  CAS  Google Scholar 

  26. G. A. Russell: J. Amer. chem. Soc. 80, 4997 (1958).

    Article  Google Scholar 

  27. C. Walling and M. F. Mayahi: J. Amer. chem. Soc. 81, 1485 (1959).

    Article  CAS  Google Scholar 

  28. H. Magritte and A. Bruylants: Ind. chim. belge 22, 547 (1957);

    CAS  Google Scholar 

  29. H. Magritte and A. Bruylants: Ind. chim. belge 51, 13735 (1957).

    Google Scholar 

  30. Z. El-Hewehi and D. Hempel: J. Prakt. Chem. [4] 22, 1 (1963).

    Article  CAS  Google Scholar 

  31. M. S. Kharasch, Y. C. Liu and W. Nudenberg: J. Org. Chem. 20, 680 (1955).

    Article  CAS  Google Scholar 

  32. M. S. Kharasch, W. Hered and F. R. Mayo: J. Org. Chem. 6, 818 (1941).

    Article  CAS  Google Scholar 

  33. J. Willard and F. Daniels: J. Amer. chem. Soc. 57, 2240 (1935).

    Article  CAS  Google Scholar 

  34. H. Schaltegger: Experientia 5, 321 (1949).

    Article  CAS  Google Scholar 

  35. H. Schaltegger: Helv. Chim. Acta 33, 2101 (1950).

    Article  CAS  Google Scholar 

  36. J. L. Speier: J. Amer. chem. Soc. 73, 826 (1951).

    Article  CAS  Google Scholar 

  37. W. Thaler: J. Amer. chem. Soc. 85, 2607 (1963).

    Article  CAS  Google Scholar 

  38. P. S. Skell and P. D. Readio: J. Amer. chem. Soc. 86, 3334 (1964).

    Article  CAS  Google Scholar 

  39. G. Hölzle and W. Jenny: Helv. Chim. Acta 41, 356 (1958).

    Article  Google Scholar 

  40. A. Roedig, in: Methoden der organischen Chemie, ed. by E. Müller, 4th ed., Vol. 5, part 4, pp. 517–678; esp. p. 530. Stuttgart: Thieme 1960.

    Google Scholar 

  41. P. S. Skell and R. R. Pavlis: J. Amer. chem. Soc. 86, 2956 (1964).

    Article  CAS  Google Scholar 

  42. B. Milligan, R. L. Bradow, J. E. Rose, H. E. Hubbert and A. Roe: J. Amer. chem. Soc. 84, 158 (1962).

    Article  CAS  Google Scholar 

  43. M. G. Voronkov and V. P. Davydova: Dokl. Akad. Nauk SSSR 125, 553 (1959);

    CAS  Google Scholar 

  44. M. G. Voronkov and V. P. Davydova: Proc. Acad. Sci. USSR, Sect. Chem. 125, 230 (1959).

    Google Scholar 

  45. E. S. Huyser and B. Giddings: J. Org. Chem. 27, 3391 (1962).

    Article  CAS  Google Scholar 

  46. H. Kloosterziel: Rec. Trav. chim. Pays-Bas 82, 497 (1963).

    Article  CAS  Google Scholar 

  47. M. F. Hebbelynck and R. H. Martin: Bull. Soc. Chim. Belges 59, 193 (1950).

    Article  CAS  Google Scholar 

  48. B. Prijs, R. Gall, R. Hinderling and H. Erlenmeyer: Helv. Chim. Acta 37, 90 (1954).

    Article  CAS  Google Scholar 

  49. S. Bernstein, L. J. Binovi, L. Dorfman, K. J. Sax and Y. Subbarow: J. Org. Chem. 14, 433 (1949).

    Article  CAS  Google Scholar 

  50. C. Meystre, A. Wettstein and K. Miescher: Helv. Chim. Acta 30, 1022 (1947).

    Article  CAS  Google Scholar 

  51. J. B. Wright: J. Amer. chem. Soc. 77, 4883 (1955).

    Article  CAS  Google Scholar 

  52. V. Oakes, H. N. Rydon and K. Undheim: J. Chem. Soc. 1962, 4678.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Technische Universität Berlin, Germany

    Alexander Schönberg

Authors
  1. Alexander Schönberg
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1968 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Schönberg, A. (1968). Photohalogenation. In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_37

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-87918-0_37

  • 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

Search

Navigation