Theoretical study on the lithium-halogen exchange reaction of 1,1-dihaloalkenes with methyllithium and the nucleophilic substitution reaction of the resulting α-halo alkenyllithiums

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 1837-1850

  Ando, Kaori ^a  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; HALOGEN COMPOUNDS; LITHIUM; ORGANIC SOLVENTS; REACTION KINETICS;

BROMINE EXCHANGE REACTION; CHLORO ALKENYLLITHIUM;

OLEFINS;

3 (2 BROMOPHENYL) 1,1 DIBROMO 1 PROPENE; 4,4 DIBROMO 3 METHYL 3 PENTENOL; ALCOHOL; ALKENE; BROMINE DERIVATIVE; HALOGEN; LITHIUM; LITHIUM DERIVATIVE; METHYLLITHIUM; PROPYLENE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; PREDICTION; PROTON TRANSPORT; SUBSTITUTION REACTION; THEORETICAL MODEL; THERMODYNAMICS;

EID: 33644640406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0519662     Document Type: Article

References (62)

1. Köbrich, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 473-485 and references therein.
2. Seebach, D.; Siegel, H.; Müllen, K.; Hiltbrunner, K. Angew. Chem., Int. Ed. 1979, 18, 784-785.
3. (a) Seebach, D.; Siegel, H.; Gabriel, J.; Hässig, R. Helv. Chim. Acta 1980, 63, 2046-2053.
4. (b) Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308-337.
5. Schleyer, P. v. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467-6475.
6. (a) Pratt, L. M.; Ramachandran, B.; Xidos, J. D.; Cramer, C. J.; Truhlar D. G. J. Org. Chem. 2002, 67, 7607-7612.
7. (b) Pratt, L. M.; Nguyen, N. V.; Le, L. T. J. Org. Chem. 2005, 70, 2294-2298.
8. Boche, G.; Marsch, M.: Müller, A.; Harms, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1032-1033.
9. (a) Köbrich, G.; Ansari, F. Chem. Ber. 1967, 100, 2011-2020.
10. (b) Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
11. (a) Braun, M. Angew. Chem., Int. Ed. Engl. 37, 430-451.
12. (b) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164-1170.
13. (c) Oku, A. J. Synth. Org. Chem., Jpn. 1995, 53, 2-12.
14. (a) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
15. (b) Eisler, S.; Tykwinski, R. R. J. Am. Chem. Soc. 2000, 122, 10736-10737.
16. (a) Harada, T.; Nozaki, Y.; Yamaura, Y.; Oku, A. J. Am. Chem. Soc. 1985, 107, 2189-2190.
17. (b) Oku, A.; Harada, T.; Hattori, K.; Nozaki, Y.; Yamaura, Y. J. Org. Chem. 1988, 53, 3089-3098.
18. Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans. 1 1991, 2575-2581.
19. (a) Negishi, E.; Akiyoshi, K.; O'Connor, B.; Takagi, K.; Wu, G. J. Am. Chem. Soc. 1989, 111, 3089-3091.
20. (b) Kasatkin, A.; Whitby, R. J. J. Am. Chem. Soc. 1999, 121, 7039-7049.
21. (a) Pelter, A.; Kvicala, J.; Parry, D. E. J. Chem. Soc., Perkin Trans. 1 1995, 2681-2682.
22. (b) Wang, B.; Deng, C. Chem. Phys. Lett. 1988, 147, 99-104.
23. (a) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1984, 106, 5035-5037.
24. (b) Topolski, M.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronska, K.; Goedken, V.; Walorsky, H. M. J. Org. Chem. 1993, 58, 546-555.
25. (c) Rachon, J.; Goedken, V.; Walborsky, H. M. J. Am. Chem. Soc. 1986, 108, 7435-7436.
26. (d) Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506-5510.
27. (a) Topolski, M. J. Org. Chem. 1995, 60, 5588-5594.
28. (b) A similar reaction of α-lithiated cyclic enol ethers was reported: Nguyen. T.; Negishi, E. Tetrahedron Lett. 1991, 32, 5903-5906.
29. (a) Yanagisawa, H.; Miura, K.; Kitamura, M.; Narasaka, K.; Ando, K. Helv. Chim. Acta 2002, 85, 3130-3135.
30. (b) Yanagisawa, H.; Miura, K.; Kitamura, M.; Narasaka, K.; Ando, K. Bull. Chem. Soc. Jpn. 2003, 76, 2009-2026.
31. 2 carbon, see: Ando, K.; Kitamura, M.; Miura, K.; Narasaka, K. Org. Lett. 2004, 6, 2461-2463 and references therein.
32. Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 552, 1-46 and references therein.
33. (a) Winkler, H. J. S.; Winkler, H. J. Am. Chem. Soc. 1966, 88, 964-969.
34. (b) Winkler, H. J. S.; Winkler, H. J. Am. Chem. Soc. 1966, 88, 969-974.
35. (c) Rogers, H. R.; Houk, J. J. Am. Chem. Soc. 1982, 104, 522-525.
36. Beak, P.; Allen D. J. J. Am. Chem. Soc. 1992, 114, 3420-3425.
37. (a) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1992, 57, 5805-5807.
38. (b) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987-8002.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuscria, 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98. revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
40. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
41. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
42. (a) Bauschlicher, C. W., Jr.; Partridge, H. J. Chem. Phys. 1995, 103, 1788-1791.
43. (b) Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
44. (a) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1989, 90, 2154-2161.
45. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
46. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622.
47. Satoh, T.; Ogino, Y.; Ando, K. Tetrahedron 2005, 61, 10262-10276.
48. (a) Abbot, A.; Streitwieser, A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1997, 119, 11255-11268.
49. (b) Ando, K. J. Org. Chem. 1999, 64, 6815-6821.
50. (c) Pratt, L. M.; Streitwieser, A. J. Org. Chem. 2003, 68, 2830-2838.
51. For the use of THF as a coordinating solvent, see: Pratt, L. M. Bull. Chem. Soc. Jpn. 2005, 78, 890-898.
52. Pople, J. A.; Head-Gordon, M. J. Chem. Phys. 1987, 87, 5968-5975.
53. Corruble, A.; Davoust, D.; Desjardins, S.; Fressigne, C.; Giessner-Prettre, C.; Harrison-Marchand, A.; Houte, H.; Lasne, M.-C.; Maddaluno, J.; Oulyadi, H.: Valnot, J.-Y. J. Am. Chem. Soc. 2002, 124, 15267-15279.
54. Schleyer, P. v. R. Pure Appl. Chem. 1984, 56, 151-162 and references therein.
55. (a) Mahler, H.; Braun, M. Tetrahedron Lett. 1987, 28, 5145-5148.
56. (b) Barluenga, J.; Rodríguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567-5568.
57. (c) Rayner, C. M.: Astles, P. C.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 3926-3936.
58. (d) Grandjean, D.; Pale, P. Tetrahedron Lett. 1993, 34, 1155-1158.
59. (e) Braun, M.; Rahematpura, J.; Bühne, C.; Paulitz, T. C. Synlett 2000, 1070-1072.
60. (f) Li, Y.; Lu, L.; Zhao, X. Org. Lett. 2004, 6, 4467-4470.
61. Ando, K. J. Am. Chem. Soc. 2005, 127, 3964-3972.
62. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.