Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3839-3843

  Eckrich, Ralf ^a   Neumann, Beate ^a   Stammler, Hans Georg ^a   Kuck, Dietmar ^a,b  

^a BIELEFELD UNIVERSITY   (Germany)

^b UNIVERSITY OF PADERBORN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344341206     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952265f     Document Type: Article

References (27)

1. This work was presented in part at the Chemiedozententagung 1993 in Dresden, Germany, Feb 28 to Mar 2, 1993; see Book of Abstracts: Kuck, D.; Eckrich, R. (Arbeitsgem. Professoreu C4 Chem.) 1993, B-19.
2. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 735 ff.
3. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186, American Chemical Society: Washington, DC, 1990.
4. For most recent reviews (and further reviews cited there) on dioxiranes, see: (a) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811.
5. (b) Adam, W.; Hadjiarapoglou, L. Top. Curr. Chem. 1993, 164, 45.
6. Parrilli, M.; Barone, G.; Adinolfi, M.; Mangoni, L. Tetrahedron Lett. 1976, 3, 207.
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8. Kuck, D. In Quasicrystals, Networks, and Molecules of Fivefold Symmetry; Hargittai, I., Ed.; VCH Publishers: New York, 1990; Chapter 19.
9. For most recent papers including a review on centropolyindans, see: (a) Kuck, D.; Schuster, A.; Paisdor, B.; Gestmann, D. J. Chem. Soc., Perkin Trans. 1 1995, 721.
10. (b) Kuck, D.; Schuster, A.; Gestmann, D.; Posteher, F.; Pritzkow, H. Chem. Eur. J. 1996, 2, 58.
11. (c) Kuck, D. Synlett 1996, in press.
12. For the oxyfunctionalization of centropolyindans with dioxiranes, see: Kuck, D.; Schuster, A.; Fusco, C.; Fiorentino, M.; Curci, R. J. Am. Chem. Soc. 1994, 116, 2375.
13. Eckrich, R.; Kuck, D. Synlett 1993, 344.
14. (a) Kuck, D.; Lindenthal, T.; Schuster, A. Chem. Ber. 1992, 125, 1449.
15. (b) Kuck, D. Angew. Chem. 1984, 96, 515. Angew. Chem., Int. Ed. Engl. 1984, 23, 508.
16. (b) Kuck, D. Angew. Chem. 1984, 96, 515. Angew. Chem., Int. Ed. Engl. 1984, 23, 508.
17. Osawa, E., Yonemitsu, Ō., Eds. Cage Hydrocarbons, Chemistry and Applications; VCH: New York, 1992.
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19. Drück, U.; Littke, W. Acta Crystallogr. B 1981, 37, 1417.
20. Epoxidation of triquinacene with dimethyldioxirane has been studied very recently: Haag, R.; de Meijere, A., to be submitted to J. Org. Chem.
21. Prefixes anti and syn denote here the orientation of the oxirane ring with respect to the triquinacene skeleton.
22. The resonances of the centro-C nucleus C(16d) and the three methine bridgehead nuclei C(4b), C(8b), and C(12b) of 5 are isochronous, as shown by using the DEPT technique.
23. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
24. Parrilli, M.; Barone, G.; Adinolfi, M.; Mangoni, L. Gaz. Chim. Ital. 1974, 104, 835.
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26. Untch, K. G.; Martin, D. J. J. Org. Chem. 1984, 29, 1903.
27. Eckrich, R. Doctoral Thesis, University of Bielefeld, 1993.