Brønsted acid mediated novel rearrangements of diarylvinylidenecyclopropanes and mechanistic investigations based on DFT calculations

Chemistry - A European Journal

Volumn 15, Issue 35, 2009, Pages 8852-8860

  Li, Wei ^a   Shi, Min ^a   Li, Yuxue ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Br nsted acids; Diarylvinylidenecyclopropanes; Lewis acids; Naphthalenes; Reaction mechanisms; Regioselectivity; Trienes

Indexed keywords

B3LYP METHOD; DFT CALCULATION; DIARYLVINYLIDENECYCLOPROPANES; GAUSSIAN03; GOOD YIELD; HIGH YIELD; LEWIS ACID; LEWIS ACIDS; MECHANISTIC STUDIES; NAPHTHALENE DERIVATIVES; REACTION MECHANISMS; RING-OPENED PRODUCTS; SOLVENT EFFECTS; SULFONIC ACID; TRIENES;

DENSITY FUNCTIONAL THEORY; NAPHTHALENE; PROBABILITY DENSITY FUNCTION; REGIOSELECTIVITY; SULFUR COMPOUNDS; TIN; TOLUENE;

ACIDS;

EID: 69749103646     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901172     Document Type: Article

References (61)

1. a) M. L. Poutsma, P. A. Ibarbia, J. Am. Chem. Soc. 1971, 93, 440-450;
2. b) W. Smadja, Chem. Rev. 1983, 83, 263-320;
3. c) M. E. Hen-drick, J.A. Hardie, M. Jones Jr, J. Org. Chem. 1971, 36, 3061-3062;
4. d) H. Sugita, K. Mizuno, T. Saito, K. Isagawa, Y. Otsuji, Tetrahedron Lett. 1992, 33, 2539-2542;
5. e) K. Mizuno, H. Sugita, T. Kamada, Y. Otsuji, Chem. Lett. 1994, 449-452, and references therein;
6. f) L. K. Sydnes, Chem. Rev. 2003, 103, 1133-1150;
7. g) T. Akasaka, Y. Misawa, W. Ando, Tetrahedron Lett. 1990, 31, 1173-1176;
8. h) K. Mizuno, H. Sugita, K. Isagawa, M. Goto, Y. Otsuji, Tetrahedron Lett. 1993, 34, 5737-5738;
9. i) K. Mizuno, K. Nire, H. Sugita, Y. Otsuji, Tetrahedron Lett. 1993, 34, 6563-6566;
10. j) K. Mizuno, H. Sugita, T. Hirai, H. Maeda, Chem. Lett. 2000, 1144-1145;
11. k) K. Mizuno, K. Hirai, H. Sugita, H. Maeda, Tetrahedron Lett. 2001, 42, 2689-2692;
12. K. Mizuno, H. Maeda, H. Sugita, S. Nishioka, T. Hirai, A. Sugimoto, Org. Lett. 2001, 3, 581-584;
13. m) K. Mizuno, H. Sugita, T. Hirai, H. Maeda, Y. Otsuji, M. Yasuda, M. Hashiguchi, K. Shima, Tetrahedron Lett. 2001, 42, 3363-3366;
14. n) H. Maeda, L. Zhen, T. Hirai, K. Mizuno, ITE Lett. Batteries, New Technol Med. 2002, 3, 485-488.
15. For the synthesis of vinylidenecyclopropanes, see : a) K. Isagawa, K. Mizuno, H. Sugita, Y. Otsuji, J. Chem. Soc. Perkin Trans 1 1991, 2283-2285, and references therein;
16. b)J.R. AlDulayymi, M.S. Baird, J. Chem. Soc. Perkin Trans. 1 1994, 1547-1548. For other papers related to vinylidenecyclopropanes,see:
17. c) H. Maeda, T. Hirai, A. Sugimoto, K. Mizuno, J. Org. Chem. 2003, 68, 7700-7706;
18. d) D. J. Pasto, J. E. Brophy, J. Org. Chem. 1991, 56, 4556-4559;
19. e) D. J. Pasto, M. F. Miles, J. Org. Chem. 1976, 41, 425-432;
20. f) D. J. Pasto, M. F. Miles, S.-K. Chou, J. Org. Chem. 1977, 42, 3098-3101;
21. g) D. J. Pasto, J. K. Borchardt, T. P. Fehlper, H. F. Baney, M. E. Schwartz, J. Am. Chem. Soc. 1976, 98, 526-529;
22. h) D. J. Pasto, A. F.T. Chen, G. Ciurdaru, L. A. Paquette, J. Org. Chem. 1973, 38, 1015-1026;
23. i) D. J. Pasto, J. K. Borchardt, J. Am. Chem. Soc. 1974, 96, 6937-6943.
24. a) G.-C. Xu, M. Ma, L.-P. Liu, M. Shi, Synlett 2005, 1869-1872;
25. b) G.-C. Xu, L.-P. Liu, J.-M. Lu, M. Shi, J. Am. Chem. Soc. 2005, 127, 14552-14553;
26. c)J.-M. Lu, M. Shi, Org. Lett. 2006, 8, 5317-5320;
27. d)Y.-P. Zhang, J.-M. Lu, G.-C. Xu, M. Shi, J. Org. Chem. 2007, 72, 509-516;
28. e)J.-M. Lu, M. Shi, Org. Lett. 2007, 9, 1805-1808;
29. f) J.-M. Lu, M. Shi, Tetrahedron 2007, 63, 7545-7549;
30. g) J.-M. Lu, M. Shi, J. Org. Chem. 2008, 73, 2206-2210;
31. h) W. Li, M. Shi, J. Org. Chem. 2009, 74, 856-860;
32. i) W. Li, M. Shi, J. Org. Chem, 2008, 73, 4151-4154;
33. J) J.-M. Lu, Z.-B. Zhu, M. Shi, Chem. Eur. J. 2009, 15, 963-971;
34. k) Z.-B. Zhu, M. Shi, Chem. Eur. J. 2008, 14, 10219-10222;
35. l) M. Shi, L.-F. Yao, Chem. Eur. J. 2008, 14, 8725-8731.
36. For the isomerization of alkenylidenecyclopropanes catalyzed by Lewis acids, see: L. Fitjer, Angew. Chem. 1975, 87, 381 -382;
37. Angew. Chem. Int. Ed. Engl. 1975, 14, 360-361.
38. [5c] a) I. A. Koppel, R. W. Taft, F. Anvia, S. Zhu, L. Hu, K. Sung, D. D. DesMarteau, L. M. Yagupolskii, Y. L. Yagupolskii, N. V. Ignat'ev, N. V. Kondratenko, A. Y. Volkonskii, V. M. Vlasov, R. Notario, P. Maria, J. Am. Chem. Soc. 1994, 116, 3047-3057;
39. b) J. Foropoulos, D. D. DesMarteau, Inorg. Chem. 1984, 23, 3720-3723;
40. a=7.0 in acetic acid at 20°C.
41. 2NH-promoted reactions, see: a) References [3h, 5b];
42. b)N. Kuhnert, J. Peverley, J. Roberston, Tetrahedron Lett. 1998, 39, 3215-3216;
43. c) K. Ishihara, Y. Hiraiwa, H. Yamamoto, Synlett 2001, 1851-1854;
44. d) J. Cossy, F. Lutz, V. Alauze, C. Meyer, Synlett 2002, 0045-0048;
45. e) K. Inanaga, K. Takasu, M. Ihara, J. Am. Chem. Soc. 2005, 127, 3668-3669;
46. f) Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B.W. Slafer, A. Davis, Org. Lett. 2005, 7, 1047-1050;
47. g) J. W. Sun, S. A. Kozmin, J. Am. Chem. Soc. 2005, 127, 13512-13513;
48. h) N. Shindoh, H. Tokuyama, K. Takasu, Tetrahedron Lett. 2007, 48, 4749-4753;
49. i) K. Takasu, Y. Miyakawa, M. Ihara, H. Tokuyama, Chem. Pharm. Bull. 2008, 56, 1205-1206;
50. j) K. Takasu, N. Shindoh, H. Tokuyama, M. Ihara, Tetrahedron 2006, 62, 11900-11907.
51. a) P. Hohenberg, W Kohn, Phys. Rev. 1964, 136, B864-B871;
52. b) W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A1133-A1138.
53. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannengerg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
54. a) A. D. Becke, Phys Rev. A 1988, 38, 3098-3100;
55. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
56. c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
57. a) M. T. Canees, V. Mennucci, J. Tomasi, J. Chem. Phys 1997, 107, 3032-3041;
58. b) M. Cossi, V. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253-263.
59. The synthesis of butatrienecyclopane 6 has been reported: a) P. J. Stang, T. E. Fisk, Synthesis 1979, 438-440;
60. b) P. J. Stang, T. E. Fisk, J. Am. Chem. Soc. 1980, 102, 6813-6816.
61. R. Ditchfield, Mol. Phys. 1974, 27, 789-807.