Diels-Alder reactions of the [60]fullerene: From regularly functionalized carbon spheres to cyclophanes

Fullerene Science and Technology

Volumn 4, Issue 2, 1996, Pages 213-226

  Maynollo, Josef ^a   Kräutler, Bernhard ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBON; CHEMICAL REACTIONS; DERIVATIVES; HYDROCARBONS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

CYCLOADDITION; CYCLOPHANES; DIELS ALDER REACTIONS; OXOHEDRAL FUNCTIONALIZATION; REGULARLY FUNCTIONALIZED CARBON SPHERES;

FULLERENES;

EID: 0030109808     PISSN: 1064122X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10641229608001548     Document Type: Article

References (62)

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9. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
10. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
11. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
12. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
13. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
14. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
15. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
16. See e.g. (a) on addition of hydrogen: Rüchardt, C., Gerst, M., Ebenhoch, J., Backhaus, H.-D., Campbell, E.E.B., Tellgmann, R., Schwarz, H., Weiske, T., and Pitter S., Angew. Chem., 1993, 105, 609; Angew. Chem., Int. Ed. Engl., 1993, 32, 584; (b) on addition of oxygen: Creegan, K.M., Robbins, J.L., Robbins, W.K., Millar, J.M., Sherwood, R.D., Tindall, P.J., Cox, D.M., Smith, A.B., III, McCauley, J.P., Jr., Jones, D.R., and Gallagher, R.T.J., Am. Chem. Soc., 1992, 114, 1103; (c) on addition of halogen: Birkett, P.R., Hitchcock, P.B., Kroto, H.W., Taylor, R., and Walton, D.R.M., Nature, 1992, 357, 479; Tebbe, F.N., Harlow, R.L., Chase, D.B., Thorn, D.L., Campbell, G.C., Jr., Calabrese, J.C., Herron, N., Young, R.J., Jr., and Wasserman, E., Science, 1992, 256, 822; (d) on addition of alkyl radicals: Krusic, P.J., Wasserman, E., Keizer, P.N., Morton, J.R., and Preston, K.F., Science, 1991, 254, 1183; (e) on addition of organometallics: see e.g.: Fagan, P.J., Calabrese, J.C., and Malone, B., Acc. Chem. Res., 1992, 25, 134; Hawkins, J.M. Acc. Chem. Res., 1992, 25, 150.
17. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
18. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
19. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
20. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
21. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
22. Representative reports on [2+1]-cycloadducts: (a) Suzuki, T., Li, Q., Khemani, K.C., and Wudl, F., J. Am. Chem. Soc., 1992, 114, 7301; (b) Smith III, A.B., Strongin R.M., Brard, L., Furst G.T., and Romanow W.J., J Am. Chem. Soc., 1993, 115, 5829; (c) Vasella, A., Uhlmann, P., Waldraff, C.A.A., Diederich, F., and Thilgen, C., Angew. Chem, 1992, 104, 1383, Angew. Chem., Int. Ed. Engl., 1992, 31, 1388; (d) Averdung, J., Luftmann, H., and Mattay, J., Tetrahedron Lett., 1995, 36, 2957; (e) Osterodt, J., Nieger, M., Windscheif, P.-M., and Vögtle, F., Chem. Ber., 1993, 126, 2331.
23. Representative reports on [2+3]-cycloadducts: (a) Prato, M., Suzuki, T., Foroudian, H., Li, Q., Khemani, K., and Wudl, F., J. Am. Chem. Soc., 1993, 115, 1594; (b) Maggini, M., Scorrano, G., Prato, M.J., Am. Chem. Soc., 1993, 115, 9798; (c) Irngartinger H., Köhler C.M., Huber-Patz, U., and Krätschmer, W., Chem. Ber., 1994, 127, 581.
24. Representative reports on [2+3]-cycloadducts: (a) Prato, M., Suzuki, T., Foroudian, H., Li, Q., Khemani, K., and Wudl, F., J. Am. Chem. Soc., 1993, 115, 1594; (b) Maggini, M., Scorrano, G., Prato, M.J., Am. Chem. Soc., 1993, 115, 9798; (c) Irngartinger H., Köhler C.M., Huber-Patz, U., and Krätschmer, W., Chem. Ber., 1994, 127, 581.
25. Representative reports on [2+3]-cycloadducts: (a) Prato, M., Suzuki, T., Foroudian, H., Li, Q., Khemani, K., and Wudl, F., J. Am. Chem. Soc., 1993, 115, 1594; (b) Maggini, M., Scorrano, G., Prato, M.J., Am. Chem. Soc., 1993, 115, 9798; (c) Irngartinger H., Köhler C.M., Huber-Patz, U., and Krätschmer, W., Chem. Ber., 1994, 127, 581.
26. Reports on [2+2]- and [2+8]-cycloadducts: (a) Hoke II, S. H:, Molstad, J., Dilettato, D., Jay, M. J., Carlson, D., Kahr, B., and Cooks, R.G., J. Org. Chem., 1992, 57, 5069; (b) Beer, E., Feuerer, M., Knorr, A., Mirlach A., and Daub, J., Angew. Chem., 1994, 106, 1140; Angew. Chem., Int. Ed. Engl., 1994, 33, 10.
27. Reports on [2+2]- and [2+8]-cycloadducts: (a) Hoke II, S. H:, Molstad, J., Dilettato, D., Jay, M. J., Carlson, D., Kahr, B., and Cooks, R.G., J. Org. Chem., 1992, 57, 5069; (b) Beer, E., Feuerer, M., Knorr, A., Mirlach A., and Daub, J., Angew. Chem., 1994, 106, 1140; Angew. Chem., Int. Ed. Engl., 1994, 33, 10.
28. Reports on [2+2]- and [2+8]-cycloadducts: (a) Hoke II, S. H:, Molstad, J., Dilettato, D., Jay, M. J., Carlson, D., Kahr, B., and Cooks, R.G., J. Org. Chem., 1992, 57, 5069; (b) Beer, E., Feuerer, M., Knorr, A., Mirlach A., and Daub, J., Angew. Chem., 1994, 106, 1140; Angew. Chem., Int. Ed. Engl., 1994, 33, 10.
29. (a) Belik, P., Gügel, A., Spickermann, J., and Müllen, K. Angew. Chem., 1993, 105, 95; Angew. Chem., Int. Ed. Engl., 1993, 32, 78;
30. (a) Belik, P., Gügel, A., Spickermann, J., and Müllen, K. Angew. Chem., 1993, 105, 95; Angew. Chem., Int. Ed. Engl., 1993, 32, 78;
31. (b) Rubin, Y., Khan, S., Freedberg, D.I., and Yeretzian, C., J. Am. Chem. Soc., 1993, 115, 344;
32. (c) Diederich, F., Jonas, U., Gramlich, V., Herrmann, A., Ringsdorf, H., and Thilgen, C., Helv. Chim. Acta, 1993, 76, 2445;
33. (d) Linssen, T.G., Dürr, K., Hanck, M., and Hirsch, A., J. Chem. Soc., Chem. Comm., 1995, 103;
34. (e) Belik, P., Gügel, A., Kraus, A., Walter M., and Müllen, K., J. Org. Chem., 1995, 60, 3307;
35. (f) Tago, T., Minowa, T., Okada, Y., and Nishimura, J., Tetrahedron Lett., 1993, 34, 8461;
36. (g) Zhang, X., and Foote, C.S., J. Org. Chem., 1994, 59, 5235.
37. (a) Kräutler, B., and Puchberger, M., Helv. Chim. Acta, 1993, 76, 1626;
38. (b) Khan, S.I., Oliver, A.M., Paddon-Row, M.N., and Rubin, Y., J. Am. Chem. Soc., 1993, 115, 4919;
39. (c) An, Y.-Z., Anderson, J.L., and Rubin, Y., J. Org. Chem., 1993, 58, 4799;
40. (d) Paquette, L.A., and Graham, R.J., J. Org. Chem., 1995, 60, 2958;
41. (e) Wilson, S.R., and Lu, Q., Tetrahedron Lett., 1993, 34, 8043.
42. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
43. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
44. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
45. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
46. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
47. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
48. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
49. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
50. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
51. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
52. See e.g.: (a) Meidine, M.F., Roers, R., Langley, G.J., Avent, A.G., Darwish, A.D., Firth, S., Kroto, H.W., Taylor, R., and Walton, D.R.M., J. Chem. Soc., Chem. Commun., 1993, 1342; (b) Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., and Lafleur, A.L., Tetrahedron Lett. 1993, 34, 1561; (c) Meidine, M.F., Avent, A.G., Darwish, A.D., Kroto, H.W., Ohashi, O., Taylor, R., and Walton. D.R., J. Chem. Soc., Perkin Trans. 2, 1994, 1189; (d) Kräutler, B., and Maynollo, J., Tetrahedron, in print; (e) Giovane, L.M., Barco, J.W., Yadav, T., Lafleur, A. L., Marr, J.A., Howard, J.B., and Rotello, V.M.; J. Phys. Chem. Soc., 1993, 97, 8560; (f) Takeshita, H., Liu, J., Kato, N., Mori, A., and Isobe, R., J. Chem. Soc., Perkin Trans I, 1994, 1433; (g) Schlueter, J.A., Seaman, J.M., Taha, S., Cohen, H., Lykke, K.R., Wang, H.H., and Williams, J.M., J. Chem. Soc., Chem. Commun. 1993, 972; h) Tsuda, M., Ishida, T., Nogami, T., Kurono, S., and Ohashi M., J. Chem. Soc., Chem. Commun. 1993, 1296; i) Ishida, T., Tsuda, M., Nogami, T., Kurono, S., and Ohashi, M., Fullerene Sci. Technol., 1994, 2, 155; j) Komatsu, K., Murata, Y., Sugita, N., Takeuchi, K., and Wan, T.S.M., Tetrahedron Lett., 1993, 34, 8473; k) Guhr, K.I., Greaves, M.D., and Rotello, V.M., J. Am.Chem. Soc., 1994, 116, 5997.
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