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.
Similar content being viewed by others
Literatur
Woodward RB, Sondheimer F, Taub D, Heusler K, McLamore WM (1951/1952) J Amer Chem Soc 73: 2403, 3546, 3548, ibid 74: 4223
Sarett LH, Arth GE, Lukes RM, Beyler BM, Poos GI, Johns WF, Constantin JM (1952) J Amer Chem Soc 74: 4974
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 Francisco
Orsini F, Pelizzoni F, Pitea D, Abbondanti E, Mugnoli A (1983) J Org Chem 48: 2866
Kato T,Kabuto C,Sasaki N,Tsunagawa M,Aizawa H,Fujita K,Kato Y,Kitahara Y (1973) Tetrahedron Lett: 3861
Corey EJ, Danheiser RL, Chandrasekaran S, Siret P, Keck GE, Gras J-L (1978) J Amer Chem Soc 100: 8031
Manning WB, Kelly TP, Muschik GM (1980) Tetrahedron Lett 21: 2629
Manning WB (1979) Tetrahedron Lett: 1661.Manning WB,Tomaszewski JE,Muschik GM,Sato RI (1977) J Org Chem 42: 3465
Kelly TR, Vaya J, Ananthasubramanian L (1980) J Amer Chem Soc 102: 5983. Dort auch eine umfangreiche Literaturzusammenstellung zu diesem Thema
VonHoff DD, Layard M, Rosencweig M, Muggia FM (1977) Cancer Treat Rep 61: 1411
Bonadonna G, Monfardini S (1969) Lancet i: 837
Goodman J, Hochstein P (1977) Biochem Biophys Res Commun 77: 797
Rama Rao AV, Deshpande VH, Laxma Reddy N (1980) Tetrahedron Lett 21: 2661
Benfaremo N, Cava MP (1985) J Org Chem 50: 139
Potman RP, Janssen NJML, Scheeren JW, Nivard RJF (1984) J Org Chem 49: 3628
Freskos JN, Morrow GW, Swenton JS (1985) J Org Chem 50: 805
Lown JW, Sondhi SM (1985) J Org Chem 50: 1413
Potman RP, van Kleef FJ, Scheeren HW (1985) J Org Chem 50: 1955
Anne A, Bennani F, Florent J-C, Moiroux J, Monneret C (1985) Tetrahedron Lett 26: 2641
Kende AS, Johnson S (1985) J Org Chem 50: 727
Kraus GA, Fulton BS (1985) J Org Chem 50: 1782
Bauman JG, Hawley RC, Rapoport H (1985) J Org Chem 50: 1569
Danishefsky SJ, Uang BJ, Quallich G (1985) J Amer Chem Soc 107: 1285
Kelly TR (Hrsg) (1984) Recent aspects of anthracyclinone chemistry. Tetrahedron Symposia-in-Print 17, Tetrahedron 40: 4537
Zee-Cheng RKY, Cheng CC (1978) J Med Chem 21: 291
Murdock KC, Child RG, Fabio PF, Angier RB, Wallace RE, Durr FE, Citarella RV (1979) J Med Chem 22: 1024
Potts KT,Bhattacharjee D,Walsh EB (1984) J Chem Soc Chem Commun: 114
Kelly TR, Gillard JW, Goerner RN, Lyding JM (1977) J Amer Chem Soc 99: 5513
Inhoffen HH, Muxfeldt H, Schaefer H, Kramer H (1957) Croat Chem Acta 29: 329
Muxfeldt H (1962) Angew Chem 74: 825
Powell VH (1970) Tetrahedron Lett: 3463.Birch AJ, Powell VH. ibid: 3467
Kelly TR (1978) Tetrahedron Lett: 1387.Kelly TR, Montury M. ibid: 4311
Boeckman RK, Dolak TM, Culos KO (1978) J Amer Chem Soc 100: 7098
Del Bene J, Jaffe HH (1968) J Chem. Phys 48: 1807
Fabian W (1985) Z Naturforsch 40a: 279
Fabian W (1985) J Mol Struct 121: 287
Rozeboom MD, Tegmo-Larsson I-M, Houk KN (1981) J Org Chem 46: 2338
Salem L (1968/1969) J Amer Chem Soc 90: 543, 553.Devaquet A, Salem L, ibid 91: 3793
Fukui K, Fujimoto H (1968) Bull Chem Soc Jap 41: 1989
Sauer J, Sustmann R (1980) Angew Chem 92: 773
Gleiter R, Böhm MC (1983) In:Watson WH (Hrsg) Stereochemistry and reactivity of systems containing π-electrons. Verlag Chemie International, Deerfield Beach, S 105
Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, Chichester, 1986
Herndon WC (1972) Chem Rev 72: 157
Pitea D, Gastaldi M, Orsini F, Pelizzoni F, Mugnoli A, Abbondanti E (1985) J Org Chem 50: 1853
Lit [42] S 150
Streitwieser A (1961) Molecular orbital theory for organic chemists. Wiley, New York, S 15
Danishefsky S, Kitahara TK (1974) J Amer Chem Soc 96: 7807
Laatsch H (1985) Liebigs Ann Chem: 251
Birch AJ,Butler DN,Siddall JB (1964) J Chem Soc: 2941
Katritzky AR, Dennis N, Chaillet M, Larrieu C, El Mouhtadi M (1979) J Chem Soc Perkin Trans 1: 408
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fabian, W. [4+2] Cycloadditionen an Chinone Eine theoretische Untersuchung zur Regioselektivität. Monatsh Chem 117, 1057–1072 (1986). https://doi.org/10.1007/BF00811276
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811276