Synthesis, x-ray crystallography, and computational analysis of 1-azafenestranes

Journal of the American Chemical Society

Volumn 128, Issue 35, 2006, Pages 11620-11630

  Denmark, Scott E ^a   Montgomery, Justin I ^a   Kramps, Laurenz A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CONFORMATIONS; OLEFINS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

1-AZAFENESTRANES; CYCLOADDITION; NITROCYCLOPENTENE; TETRAHEDRAL GEOMETRY;

PARAFFINS;

[5.5.5.5] 1 AZAFENESTRANE; AZAFENESTRANE DERIVATIVE; CYCLOPENTENE DERIVATIVE; NITROALKANE; NITROCYCLOPENTENE; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER PREDICTION; CONFORMATION; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; GEOMETRY; MOLECULAR MODEL; PRODUCT RECOVERY; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZA COMPOUNDS; BICYCLO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPROPANES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 33748357330     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0632759     Document Type: Article

References (54)

1. van't Hoff, J. H. Arch. Neert. Sci. Exactes Nat. 1874, 9, 445.
2. LeBel, J. A. Bull. Soc. Chim. Fr. 1874, 22, 337.
3. Perkin, W., Jr. Ber. Dtsch. Chem. Ges. 1884, 17, 323.
4. Eaton, P. E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1421-1436.
5. Minkin, V. I.; Minyaev, R. M.; Hoffmann, R. Russ. Chem. Rev. 2002, 71, 869-892.
6. Venepalli, B. R.; Agosta, W. C. Chem. Rev. 1987, 87, 399-410.
7. (a) Thommen, M.; Keese, R. Synlett 1997, 231-240.
8. (b) Kuck, D. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 4, pp 81-155.
9. Hirschi, D.; Luef, W.; Gerber, P.; Keese, R. Helv. Chim. Acta 1992, 75, 1897-1908.
10. (a) Han, W. C.; Takahashi, K.; Cook, J. M.; Weiss, U.; Silverton, J. V. J. Am. Chem. Soc. 1982, 104, 318-321.
11. (b) Guidetti-Grept, R.; Herzog, B.; Debrunner, B.; Siljegovic, V.; Keese, R.; Frey, H.-M.; Hauser, A.; Konig, O.; Luthi, S.; Birrer, J.; Nyffeler, D.; Fortsch, M.; Burgi, H.-B. Acta Crvstallogr., Sect. C 1995, 51, 495-497.
12. (c) Thommen, M.; Keese, R.; Fortsch, M. Acta Crystallogr., Sect. C 1996, 52, 2051-2053.
13. (d) Rao, V. B.; George, C. F.; Wolff, S.; Agosta, W. C. J. Am. Chem. Soc. 1985, 107, 5732-5739.
14. (e) Wolff, S.; Venepalli, B. R.; George, C. F.; Agosta, W. C. J. Am. Chem. Soc. 1988, 110, 6785-6790.
15. (f) Smit, W. A.; Buhanjuk, S. M.; Simonyan, S. O.; Shashkov, A. S.; Struchkov, Y. T.; Yanovsky, A. I.; Caple, R.; Gybin, A. S.; Anderson, L. G.; Whiteford, J. A. Tetrahedron Lett. 1991, 32, 2105-2108.
16. (g) Wender, P. A.; de Long, M. A.; Wireko, F. C. Acta Crystallogr., Sect. C 1997, 53, 954-956.
17. (h) Kuck, D.; Bogge, H. J. Am. Chem. Soc. 1986, 108, 8107-8109.
18. (i) Bredenkotter, B.; Florke, U.; Kuck, D. Chem. Eur. J. 2001, 7, 3387-3400.
19. (j) Dullaghan, C. A.; Carpenter, G. B.; Sweigart, D. A.; Kuck, D.; Fusco, C.; Curci, R. Organometallics 2000, 19, 2233-2236.
20. The nomenclature of Keese (ref 7a) has to be modified to specify the location of the nitrogen atom. We propose to designate its location by listing the two rings containing the nitrogen first, then proceeding to the smaller of the remaining two rings. If the two nitrogen-containing rings are of different size, the smaller will be specified first, following Keese.
21. (a) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266-8277.
22. (b) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046-3056.
23. (c) Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875-2886.
24. (d) Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887-2896.
25. (e) Denmark, S. E.; Cottell, J. J. J. Org. Chem. 2001, 66, 4276-4284.
26. For preliminary communications, see: (a) Denmark. S. E.; Kramps, L. A.; Montgomery, J. I. Angew. Chem., Int. Ed. 2002, 41, 4122-4125.
27. (b) Denmark, S. E.; Montgomery, J. I. Angew. Chem., Int. Ed. 2005, 44, 3732-3736.
28. Denmark, S. E.; Middleton, D. S. J. Org. Chem. 1998, 63, 1604-1618.
29. Seebach, D.; Calderari, G.; Knochel, P. Tetrahedron 1985, 41, 4861-4872.
30. Knochel, P.; Seebach, D. Tetrahedron Lett. 1982, 23, 3897-3900.
31. (a) Vedejs, E.; Powell, D. W. J. Am. Chem. Soc. 1982, 104, 2046-2048.
32. (b) Vedejs, E.; Gapinski, D.; Hagen, J. P. J. Org. Chem. 1981, 46, 5451-5452.
33. Clive, D. L. J.; Paul, C. C.; Wang, Z. J. Org. Chem. 1997, 62, 7028-7032.
34. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
35. (b) Barton, D. H. R.; Dorchak, J.; Jaszberenyi, J. C. Tetrahedron 1992, 48, 7435-7446.
36. (c) Robins, M. J.; Wison, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059-4065.
37. The crystallographic coordinates of 6, 46, 52, 54, 56, and 57 have been deposited with the Cambridge Crystallographic Data Centre, deposition nos. CCDC 189803, 262117, 603737, 603736, 262116, and 603735, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK; fax (+44) 1223-336-033; E-mail depo.sit@ccdc.cam.ac.uk).
38. Brunvoll, J.; Guidetti-Grept, R.; Hargittai, I.; Keese, R. Helv. Chim. Acta 1993, 76, 2838-2846.
39. In this context, it is worth mentioning that there is no intrinsic advantage to the study of azafenestranes for discerning the planarization of the central carbon compared to other substituted all-carbon fenestranes. However, the azafenestranes allow a more general approach to various ring sizes and configurations with the option of easy derivatization for crystallinity.
40. Saito, S.; Ishikawa, T.; Moriwake, T. J. Org. Chem. 1994, 59, 4375-4377.
41. (a) Hwu, J. R.; Robl, J. A.; Gilbert, B. A. J. Am. Chem. Soc. 1992, 114, 3125-3126.
42. (b) Gallos, J. K.; Stathakis, C. I.; Kotoulas, S. S.; Koumbis, A. E. J. Org. Chem. 2005, 70, 6884-6890.
43. Denmark, S. E.; Senanayake, C. B. W. Tetrahedron 1996, 52, 11579-11600.
44. Sammes, P. G.; Smith, S. J. Chem. Soc., Chem. Commun. 1983, 682-684.
45. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
46. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
47. Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3850-3856.
48. Reetz, M. T. Adv. Organomet. Chern. 1977, 16, 33.
49. The nitroso acetals 34 and 44 are derived from the different facial approaches of the dienophile to the nitrocyclopentene and give different stereochemical relationships of the ring fusion hydrogens. (Diagram presented).
50. Mitsunobu, O. Synthesis 1981, 1-28.
51. CAChe WorkSystem Pro Version 6.1.12.33; Fujitsu Ltd.: 2004.
52. Dudev, T.; Lin, C. J. Am. Chem. Soc. 1998, 120, 4450-4458.
53. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; John Wiley & Sons: New York, 2001.
54. Roux, M. V.; Dávalos, J. D.; Jiménez, P.; Notario, R.; Castano, O.; Chickos, J. S.; Hanshaw, W.; Zhao, H.; Rath, N.; Liebman, J. F.; Farivar, B. S.; Bashir-Hashemi, A. J. Org. Chem. 2005, 70, 5461-5470.