Highly strained tricyclic molecules: Tricyclo[p.q.0.01,f]alkanes and phosphatricyclo[m.1.0.01,3]alkanes

Tetrahedron

Volumn 61, Issue 10, 2005, Pages 2601-2606

  Takeuchi, Kunihiro ^a   Horiguchi, Akio ^a   Inagaki, Satoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

Strain energy; Tricyclic hydrocarbon; Tricyclic molecules; Tricyclic phosphorus molecules

Indexed keywords

ALKANE DERIVATIVE; CARBON; PHOSPHORUS;

ARTICLE; ATOM; CALCULATION; CHEMICAL REACTION; CORRELATION FUNCTION; ENERGY; HEAT; PRIORITY JOURNAL; THEORY;

EID: 13844298922     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.066     Document Type: Article

References (55)

1. M.D. Harmony, and K.W. Cox J. Am. Chem. Soc. 88 1966 5049 5050
2. K.W. Cox, and M.D. Harmony J. Chem. Phys. 50 1969 1976 1980
3. K.B. Wiberg, and F.H. Walker J. Am. Chem. Soc. 104 1982 5239 5240
4. K.B. Wiberg J. Am. Chem. Soc. 105 1983 1227 1233
5. K.B. Wiberg, W.P. Dailey, F.H. Walker, S.T. Waddell, L.S. Crocker, and M. Newton J. Am. Chem. Soc. 107 1985 7247 7257
6. K.B. Wiberg Angew. Chem., Int. Ed. Engl. 25 1986 312 322
7. K.B. Wiberg, and J.V. McClusky Tetrahedron Lett. 28 1987 5411 5414
8. K.B. Wiberg, N. McMurdie, J.V. McClusky, and C.M. Hadad J. Am. Chem. Soc. 115 1993 10653 10657
9. H. Dodziuk, J. Leszczyński, and K.S. Nowiński J. Org. Chem. 60 1995 6860 6863
10. K.B. Wiberg, and J.R. Snoonian J. Org. Chem. 63 1998 1390 1401
11. P. Gund, and T.M. Gund J. Am. Chem. Soc. 103 1981 4458 4465
12. J. March Advanced Organic Chemistry 4th ed. 1992 Wiley New York pp 150-161
13. Frisch, M. J.; Trucks, G. W. H.; Schlegel, B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3; Gaussian, Inc., Pittsburgh, PA, 2002.
14. L.A. Curtiss, K. Raghavachari, P.C. Redfern, V. Rassolov, and J.A. Pople J. Chem. Phys. 109 1998 7764 7776
15. P. George, M. Trachtman, C.W. Bock, and A.M. Brett Tetrahedron 32 1976 317 323
16. S. Inagaki, and H. Ikeda J. Org. Chem. 63 1998 7820 7824
17. See also: (b) S. Inagaki, and N. Goto J. Am. Chem. Soc. 109 1987 3234 3240
18. K. Iwase, and S. Inagaki Bull. Chem. Soc. Jpn. 69 1996 2781 2789
19. H. Ikeda, and S. Inagaki J. Phys. Chem. A 47 2001 10711 10718
20. S. Inagaki, S. Goto, and K. Yoshikawa J. Am. Chem. Soc. 51 1991 7144 7146
21. S. Inagaki, K. Yoshikawa, and Y. Hayano J. Am. Chem. Soc. 115 1993 3706 3709
22. K. Iwase, and S. Inagaki Chem. Lett. 1993 1619 1622
23. S. Inagaki, Y. Ishitani, and T. Kakefu J. Am. Chem. Soc. 116 1994 5954 5958
24. K. Iwase, S. Sakai, and S. Inagaki Chem. Lett. 1994 1601 1604
25. S. Inagaki, T. Kakefu, T. Yamamoto, and H. Wasada J. Phys. Chem. 100 1996 9615 9618
26. K. Iwase, and S. Inagaki Bull. Chem. Soc. Jpn. 69 1996 2781 2789
27. S. Inagaki, T. Yamamoto, and S. Ohashi Chem. Lett. 1997 977 978
28. S. Inagaki, S. Ohashi, and T. Kawashima Org. Lett. 1 1999 1145 1147
29. S. Inagaki, and S. Ohashi Theor. Chem. Acc. 102 1999 65 71
30. H. Ikeda, Y. Naruse, and S. Inagaki Chem. Lett. 1999 363 364
31. J. Ma, and S. Inagaki J. Phys. Chem. 104 2000 8989 8994
32. J. Ma, and S. Inagaki J. Am. Chem. Soc. 123 2001 1193 1198
33. T. Ohwada, M. Miura, H. Tanaka, S. Sakamoto, H. Ikeda, and S. Inagaki J. Am. Chem. Soc. 123 2001 10164 10172
34. H. Ikeda, N. Ushioda, and S. Inagaki Chem. Lett. 2001 166 167
35. H. Ikeda, T. Kato, and S. Inagaki Chem. Lett. 2001 270 271
36. Y. Naruse, J. Ma, and S. Inagaki Tetrahedron Lett. 42 2001 6553 6556
37. J. Ma, H. Ikeda, and S. Inagaki Bull. Chem. Soc. Jpn. 74 2001 273 278
38. Y. Naruse, S. Inagaki, N. Kano, and T. Nakagawa Tetrahedron Lett. 43 2002 5759 5762
39. J. Ma, A. Hozaki, and S. Inagaki Inorg. Chem. 41 2002 1876 1882
40. Y. Otani, O. Nagase, Y. Naruse, S. Inagaki, M. Ohno, K. Yamaguchi, G. Yamamoto, M. Uchiyama, and Y. Ohwada J. Am. Chem. Soc. 125 2003 15191 15199
41. Y. Naruse, Y. Hayashi, and S. Inagaki Tetrahedron Lett. 44 2003 8509 8512
42. Y. Naruse, J. Ma, and S. Inagaki J. Phys. Chem. A 107 2003 2860 2864
43. M. Yasui, Y. Naruse, and S. Inagaki J. Org. Chem. 69 2004 7246 7249
44. K.B. Wiberg, L.K. Olli, N. Golembeski, and R.D. Adams J. Am. Chem. Soc. 102 1980 7467 7475
45. A.R. Matlin, C.F. George, S. Wolff, and W.C. Agosta J. Am. Chem. Soc. 108 1986 3385 3394
46. L. Skattebøl J. Org. Chem. 31 1966 2789 2794
47. R. Boese, D. Bläser, K. Gomann, and U.H. Brinker J. Am. Chem. Soc. 111 1989 1501 1503
48. K.B. Wiberg, and J.R. Snoonian J. Org. Chem. 63 1998 1402 1407
49. N. Takaishi, Y. Inamoto, K. Tsuchihashi, K. Yashima, and K. Aigami J. Org. Chem. 40 1975 2929 2937
50. N. Takaishi, Y. Inamoto, Y. Fujikura, K. Aigami, B. Goličnik, K. Mlinarić-M, Z. Majerski, E. Osawa, and P.v.R. Schleyer Chem. Lett. 7 1976 763 768
51. M. Venkatachalam, G. Kubiak, J.M. Cook, and U. Weiss Tetrahedron Lett. 26 1985 4863 4866
52. K. Kakiuchi, M. Ue, H. Tsukahara, T. Shimizu, T. Miyao, Y. Tobe, Y. Odaira, M. Yasuda, and K. Shima J. Am. Chem. Soc. 111 1989 3707 3712
53. There are three different types of geminal repulsions (0.2684, 0.2810, 0.3026 au) in the envelope conformation of cyclopentane. The value is that of the corresponding geminal repulsion.
54. J.A. Boatz, and M.S. Gordon J. Phys. Chem. 93 1989 3025 3029
55. S.M. Bachrach J. Phys. Chem. 93 1989 7780 7784