Synthetic and Computational Studies on Symmetry-Defined Double Cycloaddition of a New Tris-Annulating Reagent to C60

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 5034-5041

  Isobe, Hiroyuki ^a   Tokuyama, Hidetoshi ^a   Sawamura, Masaya ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030739750     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970685u     Document Type: Article

References (83)

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33. Even double addition of a symmetrical reagent onto two double bonds on C60 would, in principle, produce the 11 structural possibilities (enantiomers inclusive) shown (black atoms indicate the carbon atoms to which X and Y groups become attached). (Matrix Presented)
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37. s derivatives: Isaacs, L.; Haldimann, R. F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2339-2342.
38. Preliminary communcation: Nakamura, E.; Isobe, H.; Tokuyama, H.; Swamura, M. J. Chem. Soc., Chem. Commun. 1996, 1747-1748.
39. For independent recent works with X = Y, see: (a) Nierengarten, J.-F.; Gramlich, V; Cardullo, F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103. (b) Shiu, L.-L.; Chien, K.-M.; Liu, T.-Y.; Lin, T.-I.; Her, G.-R.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1995, 1159-1160. Shen, C. K.-F.; Chien, K.-M.; Juo, C.-G.; Her, G.-R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 9242-9244. (c) Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926-932.
40. For independent recent works with X = Y, see: (a) Nierengarten, J.-F.; Gramlich, V; Cardullo, F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103. (b) Shiu, L.-L.; Chien, K.-M.; Liu, T.-Y.; Lin, T.-I.; Her, G.-R.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1995, 1159-1160. Shen, C. K.-F.; Chien, K.-M.; Juo, C.-G.; Her, G.-R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 9242-9244. (c) Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926-932.
41. For independent recent works with X = Y, see: (a) Nierengarten, J.-F.; Gramlich, V; Cardullo, F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103. (b) Shiu, L.-L.; Chien, K.-M.; Liu, T.-Y.; Lin, T.-I.; Her, G.-R.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1995, 1159-1160. Shen, C. K.-F.; Chien, K.-M.; Juo, C.-G.; Her, G.-R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 9242-9244. (c) Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926-932.
42. For independent recent works with X = Y, see: (a) Nierengarten, J.-F.; Gramlich, V; Cardullo, F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103. (b) Shiu, L.-L.; Chien, K.-M.; Liu, T.-Y.; Lin, T.-I.; Her, G.-R.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1995, 1159-1160. Shen, C. K.-F.; Chien, K.-M.; Juo, C.-G.; Her, G.-R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 9242-9244. (c) Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926-932.
43. For examples of useful applications of tris-annulating reagents in organic synthesis, see: Kim, B. Y.; Jeong, E, J.; Jung, W. H. J. Am. Chem. Soc. 1995, 117, 6390-6391. Winkler, J. D.; Kim, S.; Condroski, K. R.; Asensio, A.; Houk, K. N. J. Org. Chem. 1994, 59, 6879-6881. Winkler, J. D.; Holland, J. M.; Peters, D. A. J. Org. Chem. 1996, 61, 9074-9075.
44. For examples of useful applications of tris-annulating reagents in organic synthesis, see: Kim, B. Y.; Jeong, E, J.; Jung, W. H. J. Am. Chem. Soc. 1995, 117, 6390-6391. Winkler, J. D.; Kim, S.; Condroski, K. R.; Asensio, A.; Houk, K. N. J. Org. Chem. 1994, 59, 6879-6881. Winkler, J. D.; Holland, J. M.; Peters, D. A. J. Org. Chem. 1996, 61, 9074-9075.
45. For examples of useful applications of tris-annulating reagents in organic synthesis, see: Kim, B. Y.; Jeong, E, J.; Jung, W. H. J. Am. Chem. Soc. 1995, 117, 6390-6391. Winkler, J. D.; Kim, S.; Condroski, K. R.; Asensio, A.; Houk, K. N. J. Org. Chem. 1994, 59, 6879-6881. Winkler, J. D.; Holland, J. M.; Peters, D. A. J. Org. Chem. 1996, 61, 9074-9075.
46. Isaka, M.; Ejiri, S.; Nakamura, E. Tetrahedron 1992, 48, 2045-2057.
47. (a) Tokuyama, H.; Isaka M.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523-5530.
48. (b) For studies on the prototypical vinylcarbene species, see: Boger, D. L.; Brotherton, C. E. Advances in Cycloaddition, Vol. 2; JAI Press: Greenwich, CT, 1990; pp 147-219.
49. (a) Tokuyama, H.; Nakamura M.; Nakamura, E. Tetrahedron Lett. 1993, 34, 7429-7432. Tokuyama, H.; Isobe, H.; Nakamura, E. Bull. Chem. Soc. Jpn. 1995, 68, 935-941.
50. (a) Tokuyama, H.; Nakamura M.; Nakamura, E. Tetrahedron Lett. 1993, 34, 7429-7432. Tokuyama, H.; Isobe, H.; Nakamura, E. Bull. Chem. Soc. Jpn. 1995, 68, 935-941.
51. (b) For our other previous approach for organofunctionalization reactions potentially amenable to intramolecular double additions, see: Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am., Chem. Soc. 1993, 115, 1594-1595. Yamago, S.; Takeichi, A.; Nakamura, E. J. Am. Chem. Soc. 1994, 116, 1123-1124. Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754. Yamago S.; Nakamura, E. Chem. Lett. 1996, 395-396. Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380-1388.
52. (b) For our other previous approach for organofunctionalization reactions potentially amenable to intramolecular double additions, see: Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am., Chem. Soc. 1993, 115, 1594-1595. Yamago, S.; Takeichi, A.; Nakamura, E. J. Am. Chem. Soc. 1994, 116, 1123-1124. Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754. Yamago S.; Nakamura, E. Chem. Lett. 1996, 395-396. Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380-1388.
53. (b) For our other previous approach for organofunctionalization reactions potentially amenable to intramolecular double additions, see: Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am., Chem. Soc. 1993, 115, 1594-1595. Yamago, S.; Takeichi, A.; Nakamura, E. J. Am. Chem. Soc. 1994, 116, 1123-1124. Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754. Yamago S.; Nakamura, E. Chem. Lett. 1996, 395-396. Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380-1388.
54. (b) For our other previous approach for organofunctionalization reactions potentially amenable to intramolecular double additions, see: Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am., Chem. Soc. 1993, 115, 1594-1595. Yamago, S.; Takeichi, A.; Nakamura, E. J. Am. Chem. Soc. 1994, 116, 1123-1124. Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754. Yamago S.; Nakamura, E. Chem. Lett. 1996, 395-396. Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380-1388.
55. (b) For our other previous approach for organofunctionalization reactions potentially amenable to intramolecular double additions, see: Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am., Chem. Soc. 1993, 115, 1594-1595. Yamago, S.; Takeichi, A.; Nakamura, E. J. Am. Chem. Soc. 1994, 116, 1123-1124. Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754. Yamago S.; Nakamura, E. Chem. Lett. 1996, 395-396. Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380-1388.
56. The Hirsch analysis was carried out for methanofullerenes (ref 11), and the propanofullerene (specifically 8) has the same FMO pictures (see Supporting Information).
57. Haasnoot, C. A. G.; Leeuw, F. A. M. D.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
58. f = 0.1, toluene). Apparently, the double-cycloaddition reactions which leads to the formation of strained medium-size rings could not effectively compete with the reaction of the carbene species with adventitious water. (Matrix Presented)
59. 60. The first involves a case (mode 1) wherein three structural isomers, one "parallel" and two "anti-parallel" isomers, would form (ref. 13 and 14c). In the second mode of addition (mode 2), the tether stretches out perpendicular to the plane of the ring to be constructed and would give us "in-in", "in-out", and "out-out" isomers (ref 14a). (Matrix Presented)
60. We have also achieved the synthesis of the nonracemic double adduct depicted below (ref 13). Structure determination and optimization of the synthesis is currently carried out, and a full account will be reported in a due course. (Matrix Presented)
61. Herrmann, A.; Rüttimann, M.; Thilgen, C.; Diederich, F. Helv. Chim. Acta 1995, 78, 1673-1704.
62. It must also be noted that theoreticians posed questions as to the viability of the FMO theory in fullerene chemistry, where deeply seated MOs may play important roles. See: Fujimoto, H.; Nakao, Y.; Fukui, K. J. Mol. Struct. 1993, 300, 425-434. Chikama, A.; Fueno, H.; Fujimoto, H. J. Phys. Chem. 1995, 99, 8541-8549.
63. It must also be noted that theoreticians posed questions as to the viability of the FMO theory in fullerene chemistry, where deeply seated MOs may play important roles. See: Fujimoto, H.; Nakao, Y.; Fukui, K. J. Mol. Struct. 1993, 300, 425-434. Chikama, A.; Fueno, H.; Fujimoto, H. J. Phys. Chem. 1995, 99, 8541-8549.
64. Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657-1659. Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257-6265.
65. Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657-1659. Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257-6265.
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73. Since MM2* program is not energetically parameterized for organofullerenes, it will generate two types of errors upon application to the present problem. One is a global error intrinsic to fullerenes: the absolute values of the steric energy calculated, for instance, for the mono-adduct 9 are essentially useless numbers. Another error arises upon application to the double adduct 9 or 10. There is no guarantee that that the absolute values of steric energies for each isomer of W (W = A-E) can be compared with each other because energies for each isomer W may be in error.
74. These values should overestimate the conformational strain in the TS where the tether has more geometric freedom than in the product.
75. 1H NMR analysis of a solution of each analytical sample.
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