Skip to main content

Strain Release in Aromatic Molecules: The [2n] Cyclophanes

  • Chapter
Strain and Its Implications in Organic Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 273))

Abstract

The chemical behavior of the [2n] cyclophanes is determined to a large extent by strain effects.This is shown by a systematic study of isomerisation and addition reactions, respectively. In particular, the paper describes thermal, photochemical and ionic isomerisations of various [2n] cyclophanes, as well as their behavior in Diels-Alder additions, epoxidations and carbene addition reactions.

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 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
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. C.J. Brown, A. C. Farthing, Nature (London),164 (1949) 915.

    Article  CAS  Google Scholar 

  2. For recent reviews of cyclophane chemistry see

    Google Scholar 

  3. V. Boekelheide, Acc.Chem. Res., 13 (1980) 65.

    Article  CAS  Google Scholar 

  4. H. Hopf, Naturwiss., 20 (1983) 349.

    Article  Google Scholar 

  5. P.M. Keehn, S.M. Kosenfeld (eds.), The Cyclophanes, vol. I and II, Academic Press, New York, 1983.

    Google Scholar 

  6. D.J. Cram, J.M. Cram, Acc. Chem. Res., 4 (1971) 204.

    Article  CAS  Google Scholar 

  7. C.Marquard, H.Hopf, unpublished resufts.

    Google Scholar 

  8. H.J. Lindner, Tetrahedron, 32 (1976) 753.

    Article  CAS  Google Scholar 

  9. A. Greenberg, J.h. Liebman, Strained Organic Molecules, Academic Press, New York, 1978.

    Google Scholar 

  10. D.J. Cram, H.J. Reich, J.Am. Chem. Soc., 91 (1969) 3517.

    Article  Google Scholar 

  11. C.MIynek, H.Hopf, unpublished work.

    Google Scholar 

  12. H. Hopf, F.T. Lenich, Chem. Ber., 107 (1974) 1891.

    Article  CAS  Google Scholar 

  13. H. Hopf, A. E.Mourad, ChemTBer.,113 (1980) 2358, cf. D.J. Cram, E. A.Truesdale, J.Org.Chem.,45 (1980) 3974.

    Google Scholar 

  14. H. Hopf,J. Kieinschrotn, Angew. Chem.,94 (1982) 485; Angew. Chem. Int.Ed.Engl.,21 (1982) 4WT ~~

    Google Scholar 

  15. V. Boekelheide, P.F.T. Schirch, J. Am. Chem. Soc.,103 (1981) 6873.

    Article  Google Scholar 

  16. V. Boekelheide, Y. Sekine, J. Am.Chem.Soc., 103 (1981 ) 1777.

    Article  Google Scholar 

  17. G. Kaupp, E. Teufel, H. Hopf, Angew.Chem.,91 (1979) 232; Angew. Chem. Int. Ed. Engl., 18 (1979) JT5.

    Google Scholar 

  18. R. C. Helgeson, D.J.Cram, J. Am. Chem. Soc., 88 (1966) 509.

    Article  CAS  Google Scholar 

  19. H.G. Viehe, Angew. Chem., 22 (1965) 768; Angew. Chem. Int. Ed. Engl., 4 (1965J 746

    Google Scholar 

  20. B.E. van Tamelen, Angew. Chem., 22 (1965) 759; Angew. Chem. Int. Ed. Engl., 4 (1965) 738

    Google Scholar 

  21. Y. Kobayashi, T. Kumadaki, Topics Curr. Chem., 123 (1984) 103.

    CAS  Google Scholar 

  22. M. T. Reetz, S.-H. Kyung, J. Westermann, Chem. Ber., 118 (1985) 1050.

    Article  CAS  Google Scholar 

  23. J.Dannheim, H.Hopf, unpublished results, cf. J.Dannheim, Diploma thesis, Braunschweig 1985.

    Google Scholar 

  24. R.E. Oilman, M.H. Delton, D.J. Cram, J.Am. Chem. Soc., 94 (1972) 2478.

    Article  Google Scholar 

  25. D. Bryce-Smith, A. Gilbert, Tetrahedron, 32 (1976) 1309.

    Article  CAS  Google Scholar 

  26. D.J. Cram, R.C. Helgeson, D. Loch, L.A. Singer, J. Am. Chem.Soc., 88 (1966) 1324.

    Article  CAS  Google Scholar 

  27. H. Hopf, J.-H. Shin, H. Volz, Angew. Chem., 99 (1987) 594

    Article  CAS  Google Scholar 

  28. H. Hopf, J.-H. Shin, H. Volz, Angew. Chem. Int. Ed. Engl.,26 (1987) 564.

    Article  Google Scholar 

  29. H. Hopf, C.MIynek, K. broscFiinski, unpublished work, cf. K. Broschinski, Ph.d. dissertation, Braunschweig 1984.

    Google Scholar 

  30. V. Boekelheide, R.A. Hollins, J. Am. Chem. Soc., 95 (1973) 3201.

    Article  CAS  Google Scholar 

  31. J. Kleinschroth, S. El-tamany, h. Hopt, J. bruhin, Tetrahedron Lett., (1982) 3345.

    Google Scholar 

  32. V. Boekelheide, Topics Curr. Chem., 113 (1983) 87.

    CAS  Google Scholar 

  33. E. Ciganek, Tetrahedron Lett., (1967) 3321.

    Google Scholar 

  34. H.Hopf, S.Ehrhardt, unpublished work.

    Google Scholar 

  35. H. Hopf, J. Kleinschroth, A. E. Mourad, Angew. Chem., 92 (1980) 388

    Article  Google Scholar 

  36. H. Hopf, J. Kleinschroth, A. E. Mourad, Angew. Chem. Int. Ed. Engl., 19 (1980) 398

    Article  Google Scholar 

  37. K. Matsumota, I.Ukamoto, A. Sera, K. ltoh, K. Hamada, Chem. Lett., (1987) 895.

    Google Scholar 

  38. D.Wullbrandt, Ph.d. dissertation, Braunschweig 1982. We thank Prof. Dr. R. Allmann, University of Marburg, for the x-ray analyses of the epoxidation and carbene addition products.

    Google Scholar 

  39. l. Erden,P. Golitz,R. Nader,A. deMeijere, Angew. Chem.,93 (1981) 605

    Article  CAS  Google Scholar 

  40. l. Erden,P. Golitz,R. Nader,A. deMeijere, Angew. Chem. I nt. Ed. EngI., 20 (1981) 583

    Article  Google Scholar 

  41. M. Stobbe, U. Behrens, G. Adiwidiaja, P. Colitz, A. deMeijere, Angew. Chem., 95 (1980) 904

    Article  Google Scholar 

  42. M. Stobbe, U. Behrens, G. Adiwidiaja, P. Colitz, A. deMeijere, Angew. Chem. Int. Ed. Engl., 22 (1980) 867.

    Article  Google Scholar 

  43. H. Horita, T. Otsubo, Y. Sakata, S. Misumi, Tetrahedron Lett., (1976) 3899.

    Google Scholar 

  44. R. Nader, A. deMeijere, Angew.Chem., 88 (1976) 153

    Article  Google Scholar 

  45. R. Nader, A. deMeijere, Angew.Chem. Int.Ed.Engl., 15 (1976) 766

    Article  Google Scholar 

  46. H. Hopf, K. Menke, Angew.Chem., 88(1976) 152

    Article  Google Scholar 

  47. H. Hopf, K. Menke, Angew. Chem. Int. Ed.Engl., 15 (1976) 165.

    Article  Google Scholar 

  48. H.W. Whitlock, P. F. Schatz, J.Am.Chem.Soc., 93 (1971 ) 3831.

    Article  Google Scholar 

  49. K.Menke, Ph.d. dissertation, Karlsruhe 1979.

    Google Scholar 

  50. D.J. Cram, R.B. Hornby, E.A. Truesdale, H.J. Reich, M.H. Delton, J.M. Cram, Tetrahedron, 30 (1974) 1757.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Kluwer Academic Publishers

About this chapter

Cite this chapter

Hopf, H., Marquard, C. (1989). Strain Release in Aromatic Molecules: The [2n] Cyclophanes. In: de Meijere, A., Blechert, S. (eds) Strain and Its Implications in Organic Chemistry. NATO ASI Series, vol 273. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0929-8_21

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-0929-8_21

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-6907-6

  • Online ISBN: 978-94-009-0929-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics