Advertisement

Monatshefte für Chemie / Chemical Monthly

, Volume 117, Issue 8–9, pp 1057–1072 | Cite as

[4+2] Cycloadditionen an Chinone Eine theoretische Untersuchung zur Regioselektivität

  • Walter Fabian
Organische Chemie Und Biochemie

[4+2] Cycloadditions to quinones. A theoretical investigation on the regioselectivity

Abstract

Intermolecular perturbation theory has been used to treat the regioselectivity observed with [4+2] cycloadditions to quinones. Using 15 model reactions which are key steps in the synthesis of a number of biologically important natural as well as synthetic products the usefulness of this theoretical method for predicting the regioselectivity of cycloadditions is clearly demonstrated. Furthermore the various contributions to the total interaction energy are discussed in some detail.

Keywords

CNDO/S Calculations [4+2] Cycloadditions Perturbation theory Quinones 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. [1]
    Woodward RB, Sondheimer F, Taub D, Heusler K, McLamore WM (1951/1952) J Amer Chem Soc 73: 2403, 3546, 3548, ibid 74: 4223Google Scholar
  2. [2]
    Sarett LH, Arth GE, Lukes RM, Beyler BM, Poos GI, Johns WF, Constantin JM (1952) J Amer Chem Soc 74: 4974Google Scholar
  3. [3]
    Eine zusammenfassende Darstellung dazu und zu weiteren Synthesen findet sich in:Anand N, Bindra JS, Ranganathan S (1970) Art in Organic Synthesis, Holden-Day, San FranciscoGoogle Scholar
  4. [4]
    Orsini F, Pelizzoni F, Pitea D, Abbondanti E, Mugnoli A (1983) J Org Chem 48: 2866Google Scholar
  5. [5]
    Kato T,Kabuto C,Sasaki N,Tsunagawa M,Aizawa H,Fujita K,Kato Y,Kitahara Y (1973) Tetrahedron Lett: 3861Google Scholar
  6. [6]
    Corey EJ, Danheiser RL, Chandrasekaran S, Siret P, Keck GE, Gras J-L (1978) J Amer Chem Soc 100: 8031Google Scholar
  7. [7]
    Manning WB, Kelly TP, Muschik GM (1980) Tetrahedron Lett 21: 2629Google Scholar
  8. [8]
    Manning WB (1979) Tetrahedron Lett: 1661.Manning WB,Tomaszewski JE,Muschik GM,Sato RI (1977) J Org Chem 42: 3465Google Scholar
  9. [9]
    Kelly TR, Vaya J, Ananthasubramanian L (1980) J Amer Chem Soc 102: 5983. Dort auch eine umfangreiche Literaturzusammenstellung zu diesem ThemaGoogle Scholar
  10. [10]
    VonHoff DD, Layard M, Rosencweig M, Muggia FM (1977) Cancer Treat Rep 61: 1411Google Scholar
  11. [11]
    Bonadonna G, Monfardini S (1969) Lancet i: 837Google Scholar
  12. [12]
    Goodman J, Hochstein P (1977) Biochem Biophys Res Commun 77: 797Google Scholar
  13. [13]
    Rama Rao AV, Deshpande VH, Laxma Reddy N (1980) Tetrahedron Lett 21: 2661Google Scholar
  14. [14]
    Benfaremo N, Cava MP (1985) J Org Chem 50: 139Google Scholar
  15. [15]
    Potman RP, Janssen NJML, Scheeren JW, Nivard RJF (1984) J Org Chem 49: 3628Google Scholar
  16. [16]
    Freskos JN, Morrow GW, Swenton JS (1985) J Org Chem 50: 805Google Scholar
  17. [17]
    Lown JW, Sondhi SM (1985) J Org Chem 50: 1413Google Scholar
  18. [18]
    Potman RP, van Kleef FJ, Scheeren HW (1985) J Org Chem 50: 1955Google Scholar
  19. [19]
    Anne A, Bennani F, Florent J-C, Moiroux J, Monneret C (1985) Tetrahedron Lett 26: 2641Google Scholar
  20. [20]
    Kende AS, Johnson S (1985) J Org Chem 50: 727Google Scholar
  21. [21]
    Kraus GA, Fulton BS (1985) J Org Chem 50: 1782Google Scholar
  22. [22]
    Bauman JG, Hawley RC, Rapoport H (1985) J Org Chem 50: 1569Google Scholar
  23. [23]
    Danishefsky SJ, Uang BJ, Quallich G (1985) J Amer Chem Soc 107: 1285Google Scholar
  24. [24]
    Kelly TR (Hrsg) (1984) Recent aspects of anthracyclinone chemistry. Tetrahedron Symposia-in-Print 17, Tetrahedron 40: 4537Google Scholar
  25. [25]
    Zee-Cheng RKY, Cheng CC (1978) J Med Chem 21: 291Google Scholar
  26. [26]
    Murdock KC, Child RG, Fabio PF, Angier RB, Wallace RE, Durr FE, Citarella RV (1979) J Med Chem 22: 1024Google Scholar
  27. [27]
    Potts KT,Bhattacharjee D,Walsh EB (1984) J Chem Soc Chem Commun: 114Google Scholar
  28. [28]
    Kelly TR, Gillard JW, Goerner RN, Lyding JM (1977) J Amer Chem Soc 99: 5513Google Scholar
  29. [29]
    Inhoffen HH, Muxfeldt H, Schaefer H, Kramer H (1957) Croat Chem Acta 29: 329Google Scholar
  30. [30]
    Muxfeldt H (1962) Angew Chem 74: 825Google Scholar
  31. [31]
    Powell VH (1970) Tetrahedron Lett: 3463.Birch AJ, Powell VH. ibid: 3467Google Scholar
  32. [32]
    Kelly TR (1978) Tetrahedron Lett: 1387.Kelly TR, Montury M. ibid: 4311Google Scholar
  33. [33]
    Boeckman RK, Dolak TM, Culos KO (1978) J Amer Chem Soc 100: 7098Google Scholar
  34. [34]
    Del Bene J, Jaffe HH (1968) J Chem. Phys 48: 1807Google Scholar
  35. [35]
    Fabian W (1985) Z Naturforsch 40a: 279Google Scholar
  36. [36]
    Fabian W (1985) J Mol Struct 121: 287Google Scholar
  37. [37]
    Rozeboom MD, Tegmo-Larsson I-M, Houk KN (1981) J Org Chem 46: 2338Google Scholar
  38. [38]
    Salem L (1968/1969) J Amer Chem Soc 90: 543, 553.Devaquet A, Salem L, ibid 91: 3793Google Scholar
  39. [39]
    Fukui K, Fujimoto H (1968) Bull Chem Soc Jap 41: 1989Google Scholar
  40. [40]
    Sauer J, Sustmann R (1980) Angew Chem 92: 773Google Scholar
  41. [41]
    Gleiter R, Böhm MC (1983) In:Watson WH (Hrsg) Stereochemistry and reactivity of systems containing π-electrons. Verlag Chemie International, Deerfield Beach, S 105Google Scholar
  42. [42]
    Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, Chichester, 1986Google Scholar
  43. [43]
    Herndon WC (1972) Chem Rev 72: 157Google Scholar
  44. [44]
    Pitea D, Gastaldi M, Orsini F, Pelizzoni F, Mugnoli A, Abbondanti E (1985) J Org Chem 50: 1853Google Scholar
  45. [45]
    Lit [42] S 150Google Scholar
  46. [46]
    Streitwieser A (1961) Molecular orbital theory for organic chemists. Wiley, New York, S 15Google Scholar
  47. [47]
    Danishefsky S, Kitahara TK (1974) J Amer Chem Soc 96: 7807Google Scholar
  48. [48]
    Laatsch H (1985) Liebigs Ann Chem: 251Google Scholar
  49. [49]
    Birch AJ,Butler DN,Siddall JB (1964) J Chem Soc: 2941Google Scholar
  50. [50]
    Katritzky AR, Dennis N, Chaillet M, Larrieu C, El Mouhtadi M (1979) J Chem Soc Perkin Trans 1: 408Google Scholar

Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Walter Fabian
    • 1
  1. 1.Institut für Organische Chemie, Abteilung für Spektroskopie und Theoretische Organische ChemieUniversität GrazGrazÖsterreich

Personalised recommendations