Generation and reactions of pentacyclo[4.3.0.02,4.0 3,8.05,7]non-4-ene

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 2996-3005

  Forman, Mark A ^a   Moran, Caitlin ^a   Herres, Joseph P ^a   Stairs, Jason ^a   Chopko, Emily ^a   Pozzessere, Anthony ^a   Kerrigan, Michael ^a   Kelly, Carisa ^a   Lowchyj, Lisa ^a   Salandria, Kerry ^a   Gallo, Annemarie ^a   Loutzenhiser, Elizabeth ^a  

^a SAINT JOSEPH S UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; FURAN RESINS; HYDROGENATION; LITHIUM COMPOUNDS; OLEFINS;

AB INITIO CALCULATIONS; OLEFIN STRAIN ENERGY; PYRAMIDALIZED ALKENES; PYRAMIDALIZED DOUBLE BOND;

REACTION KINETICS;

ALKENE DERIVATIVE; ALKYL GROUP; BENZOFURAN DERIVATIVE; CYCLOALKANE DERIVATIVE; FURAN DERIVATIVE; LITHIUM DERIVATIVE; SPIRO COMPOUND;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; DIELS ALDER REACTION; ENERGY; HYDROGENATION; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

ALKENES; HETEROCYCLIC COMPOUNDS; ISOMERISM; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; THERMODYNAMICS;

EID: 34247194276     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0626313     Document Type: Article

References (71)

1. Weinshenker, N. M.; Greene, F. D. J. Am. Chem. Soc. 1968, 90, 506.
2. Szeimies, G. Chimia 1981, 35, 243.
3. (a) Borden, W. T. Synlett 1996, 711.
4. (b) Borden, W. T. Chem. Rev. 1989, 89, 1095.
5. Luef, W.; Keese, R. Top. Stereochem. 1991, 20, 231.
6. Vazquez, S.; Camps, P. Tetrahedron 2005, 61, 5147.
7. See, for example: (a) Rasul, G.; Olah, G. A.; Prakash, G. K. S. J. Phys. Chem. A 2006, 110, 7197.
8. (b) Williams, R. V.; Margetic, D. J. Org. Chem. 2004, 69, 7134.
9. (c) Margtic, D.; Williams, R. V.; Warrener, R. N. J. Org. Chem. 2003, 68, 9186.
10. (d) Can, H.; Zahn, D.; Baici, M.; Brickmann, J. Eur. J. Org. Chem. 2003, 1111.
11. (e) Vazquez, S. J. Chem. Soc., Perkin Trans. 2002, 2, 2100.
12. (f) Yates, B. F. J. Organomet. Chem. 2001, 635, 142.
13. (g) Mastryukov, V. S.; Chen, K.-H.; Allinger, N. L. J. Phys. Chem. A 2001, 105, 8562.
14. (h) Mastryukov, V. S.; Boggs, J. E. Struct. Chem. 2000, 11, 97.
15. Borden has extensively reviewed the chemistry of the syn- sesquinorbornenes; see ref 3b. For selected additional examples, see: (a) Griesbeck, A. G.; Deufel, T.; Hohlneicher, G.; Rebentisch, R.; Steinwascher, J. Eur. J. Org. Chem. 1998, 1759.
16. (b) Holthausen, M. C.; Koch, W. J. Phys. Chem. 1993, 97, 10021.
17. (c) Paquette, L. A.; Shen, C. C. J. Am. Chem. Soc. 1990, 112, 1159.
18. (d) Paquette, L. A.; Shen, C. C.; Krause, J. A. J. Am. Chem. Soc. 1989, 111, 2351.
19. (e) Spanget-Larsen, J.; Gleiter, R. Tetrahedron 1983, 39, 3345.
20. (a) Lukin, K.; Eaton, P. E. J. Am. Chem. Soc. 1995, 117, 7652.
21. (b) Staneke, P. O.; Ingemann, S.; Eaton, P.; Nibbering, N. M. M.; Kass, S. R. J. Am. Chem. Soc. 1994, 116, 6445.
22. (c) Eaton, P. E.; Maggini, M. J. Am. Chem. Soc. 1988, 110, 7230.
23. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1988, 110, 7229.
24. Schaefer, J.; Szeimies, G. Tetrahedron Lett. 1988, 29, 5253.
25. Rosendorfer, K.; Jarosch, O.; Polborn, K.; Szeimies, G. Liebigs Ann. 1995, 1765.
26. Marchand, A. P.; Namboothiri, I. N. N.; Ganguly, B.; Watson, W. H.; Bodige, S. G. Tetrahedron Lett. 1999, 40, 5105.
27. (a) Theophanous, F. A.; Tasiopoulos, A. J.; Nicolaides, A.; Zhou, X.; Johnson, W. T. G.; Borden, W. T. Org. Lett. 2006, 8, 3001.
28. (b) Smith, J. M.; Hrovat, D. A.; Borden, W. T.; Allan, M.; Asmis, K. R.; Bulliard, C.; Haselbach, E.; Meier, U. C. J. Am. Chem. Soc. 1993, 115, 3816.
29. (c) Branan, B. M.; Paquette, L. A.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1992, 114, 774.
30. (d) Renzoni, G. E.; Yin, T. K.; Borden, W. T. J. Am. Chem. Soc. 1986, 108, 7121 and references cited therein and in ref 3.
31. (a) Camps, P.; Munoz, M. R.; Vazquez, S. J. Org. Chem. 2005, 70, 1945.
32. (b) Camps, P.; Fernández, J. A.; Font-Bardia, M.; Solans, X.; Vázquez, S. Tetrahedron 2005, 61, 3593.
33. (c) Camps, P.; Fernández, J. A.; Vázquez, S.; Font-Bardia, M.; Solans, X. Angew. Chem., Int. Ed. 2003, 42, 4049.
34. (d) Camps, P.; Luque, F. J.; Orozco, M.; Pérez, F.; Vázquez, S. Tetrahedron Lett. 1996, 37, 8605.
35. (e) Camps, P.; Font-Bardia, M.; Pérez, F.; Solans, X.; Vázquez, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 912 and references cited therein and in ref 5.
36. See: Reinbold, J.; Sackers, E.; Osswald, T.; Weber, K.; Weiler, A.; Voss, T.; Hunkler, D.; Worth, J.; Knothe, L.; Sommer, F.; Morgner, N.; Von Issendorff, B.; Prinzbach, H. Chem.-Eur. J. 2002, 8, 509 and references cited therein.
37. See, for example: (a) Lee, G.-A.; Huang, A. N.; Chen, C.-S.; Li, Y. C.; Jann, Y.-C. J. Org. Chem. 1997, 62, 3355.
38. (b) Chenier, P. J.; Bauer, M. J.; Hodge, C. L. J. Org. Chem. 1992, 57, 5959.
39. (c) Wiberg, K. B.; Artis, D. R.; Bonneville, G. J. Am. Chem. Soc. 1991, 113, 7969.
40. (d) Chenier, P. J.; Southard, D. A., Jr. J. Org. Chem. 1989, 54, 3519.
41. (e) Wiberg, K. B.; Bonneville, G. Tetrahedron Lett. 1982, 23, 5385.
42. (f) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI: Greenwich, 1992; Vol. 2. p 1.
43. (a) Szeimies, G. J. Prakt. Chem./Chem.-Ztg. 1998, 340, 11.
44. (b) Rosendorfer, K.; Jarosch, O.; Polborn, K.; Szeimies, G. Liebigs Ann. 1995, 1765.
45. (c) Podlech, J.; Polborn, K.; Szeimies, G. J. Org. Chem. 1993, 58, 4113.
46. (d) Heywang, U.; Szeimies, G. Chem. Ber. 1990, 123, 121.
47. (e) Harnisch, J.; Baumgaertel, O.; Szeimies, G.; Van Meerssche, M.; Germain, G.; Declercq, J. P. J. Am. Chem. Soc. 1979, 101, 3370.
48. Kenndoff, J.; Polborn, K.; Szeimies, G. J. Am. Chem. Soc. 1990, 112, 6117.
49. Dolbier, W. R., Jr.; Zhai, Y.-A.; Battiste, M. A.; Abboud, K. A.; Ghiviriga, I. J. Org. Chem. 2005, 70, 10336.
50. (a) Huebner, C. F.; Donoghue, E.; Dorfman, L.; Wenkert, E.; Streth, W. E.; Donely, S. W. Chem. Commun. 1966, 419.
51. (b) Prinzbach, H.; Hunkler, D. Angew. Chem., Int. Ed. Engl. 1967, 6, 247.
52. Moriarty, R. M.; Khosrowshahi, J. S.; Dalecki, T. M. J. Chem. Soc., Chem. Commun. 1987, 675.
53. Concepcion, J. I.; Francisco, C. G.; Freire, R.; Hernandez, R.; Salazar, J. A.; Suarez, E. J. Org. Chem. 1986, 51, 402.
54. Arts, N. B. M.; Weenen, H.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1983, 39, 2825.
55. Tsanaktsidis, J.; Eaton, P. E. Tetrahedron Lett. 1989, 30, 6967.
56. See, for example: (a) Camps, P.; Munoz, M. R.; Vázquez, S. Tetrahedron 2006, 62, 7645.
57. (b) Camps, P.; Font-Bardia, M.; Mendez, N.; Perez, F.; Pujol, X.; Solans, X.; Vázquez, S.; Vilalta, M. Tetrahedron 1998, 54, 4679.
58. (c) Branan, B. M.; Paquette, L. A.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1992, 114, 774 and refs 9, 10, and 14a.
59. This yield represents the lower bound, as 27 rearranges upon purification via flash column chromatography, even when the eluent contains 2% triethylamine to deactivate the silica gel.
60. We are grateful to Professor William Bailey (University of Connecticut) for calling our attention to the importance of this solvent for effecting lithium-iodine exchange with tert-butyllithium. See: J. Org. Chem. 1990, 55, 5404.
61. (a) Herres, J. P.; Forman, M. A.; Wheeler, K. A. Acta Crystallogr., Sect. E 2005, E61, o3961.
62. (b) Herres, J. P.; Forman, M. A.; Wheeler, K. A.; Yap, G. P. A. Acta Crystallogr., Sect. E 2005, E61, o1223. We also observe this same reaction with n-butyllithium.
63. See, for example, refs 16 and 17.
64. Hamlin, J. E.; Toyne, K. J. J. Chem. Soc., Perkin Trans. 1981, 1, 2731.
65. Craciun, L.; Jackson, J. E. J. Phys. Chem. A 1998, 102, 3738.
66. C-H and the % s character in the carbon hybrid orbital, as proposed by Muller and Pritchard. (a) Muller, N.; Pritchard, D. E. J. Chem. Phys. 1959, 31, 1471.
67. (b) Muller, N.; Pritchard, D. E. J. Chem. Phys. 1959, 31, 768.
68. Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44, 449.
69. See, for example, refs 6f and 14a-c.
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
71. Schleyer, P. v. R.; Maier, W. F. J. Am. Chem. Soc. 1981, 103, 1891.