Toward selective reactions with C-H bonds: A rationale for the regio- and stereochemistry of dichlorocarbene insertions into cyclic hydrocarbons

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 10211-10219

  Mieusset, Jean Luc ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRIDE TRANSFER POTENTIAL (HTP); NUCLEOPHILIC-ELECTROPHILIC MECHANISM;

DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; REACTION KINETICS; STEREOCHEMISTRY;

HYDROCARBONS;

ALKANE; CARBENE; CARBENOID; CARBON; CATION; DICHLOROCARBENE; HYDROCARBON; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; COMPARATIVE STUDY; DENSITY FUNCTIONAL THEORY; EXPERIMENTAL STUDY; FRAGMENTATION REACTION; HYDROGEN BOND; MOLECULE; PREDICTION; REACTION ANALYSIS; STEREOCHEMISTRY;

HYDROCARBONS, CHLORINATED; HYDROCARBONS, CYCLIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 37549061839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702047b     Document Type: Article

References (84)

1. (a) Hill, C. L., Ed. Activation and Functionalization of Alkanes; Wiley: New York, 1989.
2. (b) Davies, J. A.; Watson, P. L.; Liebman, J. F.; Greenberg, A. Selective Hydrocarbon Activation: Principles and Progress; VCH Publishers: New York, 1990.
3. Barton, D. H. R. Aldrichim. Acta 1990, 23, 3-10.
4. (a) Dehmlow, E. V. In Houben-Weyl (Methoden der Organischen Chemie); Regitz, M., Ed.; Thieme: Stuttgart, 1989; Vol. E 19b, 1521-1589.
5. (b) Masaki, Y.; Arasaki, H.; Shiro, M. Chem. Lett. 2000, 29, 1180.
6. (c) Masaki, Y.; Arasaki, H.; Iwata, M. Chem. Lett. 2003, 32, 4.
7. (d) Arasaki, H.; Iwata, M.; Makida, M.; Masaki, Y. Chem. Pharm. Bull. 2004, 52, 848.
8. (e) Zlotskii, S. S.; Bazunova, G. G.; Mikhailova, N. N. Bashk. Khim. Zh. 2005, 12, 21.
9. (f) Masaki, Y. Gifu Yakka Daigaku Kiyo 2005, 54, 29.
10. (a) Jones, W. M.; Brinker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. 1, p 118.
11. (b) Dobson, R. C.; Hayes, D. M.; Hoffmann, R. J. Am. Chem. Soc. 1971, 93, 6188.
12. (c) Bodor, N.; Dewar, M. J. S. J. Am. Chem. Soc. 1972, 94, 9103.
13. (d) Bodor, N.; Dewar, M. J. S.; Wasson, J. S. J. Am. Chem. Soc. 1972, 94, 9095.
14. (e) Raghavachri, K.; Chandrasekhar, J.; Gordon, M. S.; Dykema, K. J. J. Am. Chem. Soc. 1984, 106, 5853.
15. (f) Gordon, M. S.; Gano, D. R. J. Am. Chem. Soc. 1984, 106, 5421.
16. (g) Gordon, M. S.; Boatz, J. A.; Gano, D. R.; Friederichs, M. G. J. Am. Chem. Soc. 1987, 109, 1323.
17. (h) Cremaschi, P.; Simonetta, M. J. Chem. Soc. Faraday Trans. 11 1974, 1801.
18. (i) Gano, D. R.; Gordon, M. S.; Boatz, J. A. J. Am. Chem. Soc. 1991, 113, 6711.
19. (j) Sosa, C.; Schlegel, H. B. J. Am. Chem. Soc. 1984, 106, 5847.
20. (k) Lin, Q.- J.; Feng, D.-C.; Qi, C.-S. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1922.
21. (l) Feng, D.-C.; Lin, Q.-J.; Ma, W.-Y.; Wang, H.-J. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1708.
22. (m) Lin, Q.-J.; Feng, D.-C.; Ma, W.-Y. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1427.
23. (n) Lin, Q.-J.; Feng, D.-C.; Qi, C.-S. Jiegou Huaxue 2000, 19, 224.
24. Bach, R. D.; Su, M.-D.; Aldabbagh, E.; Andrés, J. L.; Schlegel, H. B. J. Am. Chem. Soc. 1993, 115, 10237.
25. Sevin, F.; McKee, M. L.; Shevlin, P. B. J. Org. Chem. 2004, 69, 382.
26. Ramalingam, M.; Ramasami, K.; Venuvanalingam, P. Chem. Phys. Lett. 2006, 430, 414.
27. See also: Ramalingam, M.; Ramasami, K.; Venuvanalingam, P.; Sethuraman, V. THEOCHEM 2005, 755, 169.
28. (a) Xu, L.; Tao, F.; Yu, T. Acta Chim. Sinica, Engl. Ed. 1987, 294.
29. (b) Xu, L.; Tao, F.; Yu, T. Acta Chim. Sinica, Chin. Ed. 1988, 46, 608;
30. Chem. Abstr. 1988, 109, 189862r.
31. (c) Xu, L.; Tao, F. Synth. Commun. 1988, 2117.
32. (d) Xu, L.; Lin, G.; Tao, F.; Brinker, U. H. Acta Chem. Scand. 1992, B46, 650.
33. (e) Xu, L.; Brinker, U. H. In Synthetic Organic Sonochemistry; Luche, J.-L., Ed.; Plenum Press: New York, 1998; pp 344-345.
34. (a) Xu, L.; Smith, W. B.; Brinker, U. H. J. Am. Chem. Soc. 1992, 114, 783.
35. (b) Brinker, U. H.; Lin, G.; Xu, L.; Smith, W. B.; Mieusset, J.-L. J. Org. Chem. 2007, 72, 8434.
36. (a) Carreira, L. A.; Lord, R. C. J. Chem. Phys. 1969, 51, 2735.
37. (b) Lord, R. C.; Malloy, T. B., Jr. J. Mol. Spectrosc. 1973, 46, 358.
38. (c) Lewis, J. D.; Laane, J.; Malloy, T. B., Jr. J. Chem. Phys. 1974, 61, 2342.
39. (d) Cook, R. L.; Malloy, T. B., Jr. J. Am. Chem. Soc. 1974, 96, 1703.
40. (e) Mastryukov, V. S.; Osina, E. L.; Vilkov, L. V.; Hilderbrandt, R. L. J. Am. Chem. Soc. 1977, 99, 6855.
41. (f) Choo, J.; Chiang, W. Y.; Lee, S. N.; Laane, J. J. Phys. Chem. 1995, 99, 11636.
42. Kang, P.; Choo, J.; Jeong, M.; Kwon, Y. J. Mol. Struct. 2000, 519, 75.
43. See also: (a) Skancke, P. N. THEOCHEM 1982, 86, 255.
44. (b) Siam, K.; Ewbank, J. D.; Schäfer, L.; Van Alsenoy, C. THEOCHEM 1987, 150, 121.
45. (c) Okazaki, R.; Niwa, J.; Kato, S. Bull. Chem. Soc. Jpn. 1988, 61, 1619.
46. (d) Shen, Q.; Mastryukov, V. S.; Boggs, J. E. J. Mol. Struct. 1995, 352/353, 181.
47. -1, allowing a direct comparison of the activation enthalpies.
48. (a) Brook, P. R.; Ellam, R. M.; Bloss, A. S. Chem. Commun. 1968, 8, 425.
49. (b) Bloss, A. S.; Brook, P. R.; Ellam, R. M. J. Chem. Soc, Perkin Trans. 2 1973, 15, 2165.
50. (c) Jorgensen, W. L. Tetrahedron Lett. 1976, 35, 3029.
51. (d) Mjoberg, P. J.; Almlof, J. Chem. Phys. 1978, 29, 201.
52. (e) Szabo, K. J.; Kraka, E.; Cremer, D. J. Org. Chem. 1996, 61, 2783.
53. (a) Naumov, V. A; Bezzubov, V. M. Proc. Acad. Sci. USSR 1970, 193, 477.
54. (b) Wiberg, K. B.; Bonneville, G.; Dempsey, R. Isr. J. Chem. 1983, 23, 85.
55. (a) Alabugin, I. V.; Zeidan, T. A. J. Am. Chem. Soc. 2002, 124, 3175.
56. (b) Alabugin, I. V.; Manoharan, M. J. Org. Chem. 2004, 69, 9011.
57. (a) Yoshida, Z.; Tabushi, I.; Takahashi, N. J. Am. Chem. Soc. 1970, 92, 6670.
58. (b) Slobodin, Y. M.; Ashkinazi, L. A.; Klimchuk, G. N. Zh. Org. Khim. 1984, 20, 1238.
59. Dehmlow, E. V. Tetrahedron 1971, 27, 4071.
60. Seyferth, D.; Burlitch, J. M. J. Am. Chem. Soc. 1963, 85, 2667.
61. Chu, G.; Moss, R. A.; Sauers, R. R. J. Am. Chem. Soc. 2005, 127, 14206.
62. Seyferth, D.; Burlitch, J. M. J. Am. Chem. Soc. 1964, 86, 2730.
63. (a) Starks, C. M. J. Am. Chem. Soc. 1971, 93, 195.
64. (b) Dehmlow, E. V. Justus Liebigs Ann. Chem. 1972, 148.
65. (a) Roberts, J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 3542.
66. (b) Koch, W.; Liu, B.; DeFrees, D. J. J. Am. Chem. Soc. 1988, 110, 7325.
67. (c) Saunders, M.; Laidig, K. E.; Wiberg, K. B.; Schleyer, P. v. R. J. Am. Chem. Soc. 1988, 110, 7652.
68. (d) Wiberg, K. B.; Shobe, D.; Nelson, G. L. J. Am. Chem. Soc. 1993, 115, 10645.
69. (e) Cacace, F.; Chiavarino, B.; Crestoni, M. E. Chem. Eur. J. 2000, 6, 2024.
70. Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
71. (a) Kötz, A.; Zörnig, W. J. Prakt. Chem. 1906, 74, 425.
72. (b) Krapcho, A. P. J. Org. Chem. 1962, 27, 2375.
73. (c) Kira, M. A.; Osman, A. I.; Kamel, O. K. Egypt. J. Chem. 1980, 20, 557.
74. (a) Jackson, J. E.; Mock, G. B.; Tetef, M. L.; Zheng, G.-X.; Jones, M., Jr. Tetrahedron 1985, 41, 1453.
75. (b) Koptelov, Y. B.; Kostikov, R. R.; Molchanov, A. P. Zh. Org. Khim. 1991, 27, 1902.
76. (c) Xu, L.; Miebach, T.; Brinker, U. H.; Smith, W. B. Tetrahedron Lett. 1991, 32, 4461.
77. (d) Rablen, P. R. 38th Middle Atlantic Regional Meeting of the American Chemical Society, Hershey, PA, June 4-7, 2006.
78. (a) Freeman, P. K.; Pugh, J. K. J. Org. Chem. 2000, 65, 6107.
79. (b) Freeman, P. K.; Dacres, J. E. J. Org. Chem. 2003, 68, 1386.
80. 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.; 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; Gaussian, Inc.: Pittsburgh, PA, 2003.
81. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
82. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
83. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
84. Masamune, S.; Sakai, M.; Kemp-Jones, A. V.; Nakashima, T. Can. J. Chem. 1974, 52, 855.