Abstract
During the last recent years fullerenes and their derivatives have shown a wide variety of interesting properties and applications. Most of these modified fullerenes have been prepared by different chemical approaches developed during the last decade. The most important chemical methodologies designed for the synthesis of novel organofullerenes will be presented in the first chapters of this book for a better understanding of the importance that synthetic aspects have in the search of novel properties and applications of functionalized fullerenes.
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References
Hirsch, A., Ed., “Fullerenes and Related Structures”, in Topics in Current Chemistry, Springer: Berlin, 1998; Vol. 199.
See, for example: a) “Comprehensive Organic Chemistry”, Paquette L.A., Ed.; Pergamon: New York, 1991
Afarinkia K., Vinader V., Nelson T.D. and Posner G.H. (1992) Tetrahedron 48, 9111; c) Luh T.-Y. and Wong K.-T. (1993) Synthesis, 349
Barluenga J., Tomas M. “Synthesis of Heterocyclics from Azadienes” in Adv. Heterocycl. Chem., Katritzky A.R., Ed., Academic: San Diego, 1993, Vol. 57, pp. 1–80
Bols M. (1995) Chem. Rev. 95, 1253
Behforouz M. and Ahmadian M. (2000) Tetrahedron 56, 5259.
Houk K.N. and Gonzalez J., Li Y. (1995) Acc. Chem. Res. 28, 181
Dewar M.J.S., Santiago O. and Stewart J.J.P. (1986) J. Am. Chem. Soc. 108, 5771
Sauer J. and Sustmann R. (1980) Angew. Chem. Int. Ed. Engl. 19, 779.
Eksterowicz J.E. and Houk K.N. (1993) Chem. Rev. 93, 2439
Houk K.N., Li Y. and Evanseck J.D. (1992) Angew. Chem. Int. Ed. Engl. 31, 682.
Khan S.I., Oliver A.M., Paddon-Row M.N. and Rubin Y. (1993) J. Am. Chem. Soc. 115, 4919.
Diederich F., Jonas U., Gramlich V., Herrmann A., Ringsdorf H. and Thilgen C. (1993) Helv. Chim. Acta 76, 2445.
Chikama A., Fueno H. and Fujimoto H. (1995) J. Phys. Chem. 99, 8541.
Sola M., Durán M. and Mestres J. (1996) J. Am. Chem. Soc. 118, 8920.
Mestres J., Durán M. and Sola M. (1996) J. Phys. Chem. 100, 7449.
Hirsch A. (1995) Synthesis, 895.
Houk K.N., Li Y. and Evanseck J.D. (1992) Angew. Chem. Int. Ed. Engl. 31, 682.
Chronakis N. and Orfanopoulos M. (2001) Tetrahedron Lett. 42, 1201
Chronakis N. and Orfanopoulos M. (2001) Org. Lett. 3, 545.
Mikami K., Matsumoto S., Okubo Y., Fujitsuka M., Ito O., Suenobu T. and Fukuzumi S. (2000) J. Am. Chem. Soc. 122, 2236; b) Mikami K., Matsumoto S., Okubo Y., Suenobu T. and Fukuzumi S. (1999) Synlett., 1130.
Sustmann R., Lücking K., Kopp G. and Rese M. (1989) Angew. Chem. Int. Ed. Engl. 28, 1713.
See, for example: a) Hirsch A. “The Chemistry of Fullerenes”, Thieme: Stuttgart, 1994
Taylor R. “Lecture Notes on Fullerene Chemistry. A Handbook for Chemists”, Imperial College Press, London, 1999
Diederich F. and Thilgen C. (1996) “Covalent Fullerene Chemistry”, Science 271, 317.
Meidine M.F., Roers M., Langley G.J., Avent A.G., Darwish A.D., Firth S., Kroto H.W., Taylor R. and Walton D.R.M. (1993) J. Chem. Soc. Chem. Commun., 1342.
Wilson S.R., Yurchenko M.E. and Schuster D.I. (2000) J. Org. Chem. 65, 2619.
Martinez R., Herrera A., Martin N., Gonzalez, B. and Illescas B. (1998) Rapid Comm. in Mass Spect. 12, 568.
Ohno M., Kojima S., Shirakawa Y. and Eguchi S. (1995) Tetrahedron Lett. 36, 6899
Illescas B., Martin N., Seoane C., De la Cruz P., Langa F. and Wudl F. (1995) Tetrahedron Lett. 36, 8307
Fernandez-Paniagua U.M., Illescas B., Martin N., Seoane C., De la Cruz P., De la Hoz A. and Langa F. (1997) J. Org. Chem. 62, 3705.
Herrmann A., Diederich F., Thilgen C., Ter Meer H.-U. and Müller W.H. (1994) Helv. Chim. Acta 77, 1689
Balch A.L., Ginwalla A.S., Lee J.W., Noll B.C. and Olmstead M.M. (1994) J. Am. Chem. Soc. 116, 2227; c) Meier M.S., Guarr T.F., Selegue J.P. and Vance V.K. (1993) J. Chem. Soc., Chem. Commun., 63.
Nie B., Hasan K., Greaves M.D. and Rotello V.M. (1995) Tetrahedron Lett. 36, 3617.
González R., Knight B.W., Wudl F., Semones M.A. and Padwa A. (1994) J. Org. Chem. 59, 7949.
An Y.-Z., Ellis G.A., Viado A.L. and Rubin Y. (1995) J. Org. Chem. 60, 6353.
As a recent review, see: Diederich F. and Kessinger R. (1999) Acc. Chem. Res. 32, 537.
Cardullo F., Isaacs L., Diederich F., Gisselbrecht J.-P., Boudon C. and Gross M. (1996) Chem. Commun., 797.
Qian W. and Rubin Y. (1999) Angew. Chem. Int. Ed. 38, 2356.
Cardullo F., Seiler P., Isaacs L., Nierengarten J.F., Haldimann R.F., Diederich F., Mordasini-Denti T., Tiel W., Boudon C., Gisselbrecht J.P. and Gross M. (1997) Helv. Chim. Acta 80, 343.
Kraüler B. and Maynollo J. (1996) Tetrahedron 52, 5033.
Komatsu K., Murata Y., Miyabo A., Takeuchi T. and Wan T.S.M. (1993) Fullerene Sci & Technol. 1, 231
Komatsu K., Murata Y., Sugita N., Takeuchi K. and Wan T.S.M. (1993) Tetrahedron Lett. 34, 8473.
Schieuter J.A., Seaman J.H., Taha S., Cohen H., Lykke K.R., Wang H.H. and Williams J.M. (1993) J. Chem. Soc., Chem. Commun., 972.
Tsuda M., Akayuki T., Nogami T., Kurono S. and Ohashi M. (1993) J. Chem. Soc., Chem. Commun., 1296.
Wudl F. (1992) Acc. Chem. Res. 25, 157.
Kräutler B., Müller T., Maynollo J., Gruber K., Kratky C., Ochsenbein P., Schwarzenbach D. and Bürgi H.-B. (1996) Angew. Chem.Int. Ed. Engl. 35, 1204.
Avent A.G., Birkett P.R., Darwish A.D., Kroto H.W., Taylor R. and Walton D.M.R. (1997) Fullerene Sci. & Technol. 5, 643.
Avent A.G., Boltalina O.V., Street J.M., Taylor R. and Wei X.-W. (2001) J. Chem. Soc., Perkin Trans. 2, 994.
Schwenninger R., Müller T. and Kräutler B. (1997) J. Am. Chem. Soc. 119, 9317.
Duarte-Ruiz A., Müller T., Wurst K. and Kräutler B. (2001) Tetrahedron, 3709.
Lamparth I., Maichle-Mössmer C. and Hirsch A. (1995) Angew. Chem. Int. Ed. Engl. 34, 1607.
Wang G.-W., Saunders M. and Cross J. (2001) J. Am. Chem. Soc. 123, 256.
Hummelen J.C., Prato M. and Wudl F. (1995) J. Am. Chem. Soc. 117, 7003
Hummelen J.C., Knight B., Pavlovich J., González R. and Wudl F. (1995) Science 269, 1554.
Birkett P.R., Avent A.G., Darwish A.D., Kroto H.W., Taylor R. and Walton D.R.M. (1995) J. Chem. Soc., Chem. Commun., 1869.
Schick G., Hirsch A., Mauser H. and Clark T. (1996) Chem. Eur. J. 2, 935; b) Shiu L.L., Chien K.M., Liu T.Y., Lin T.I., Her G.R. and Luh T.Y. (1995) J. Chem. Soc., Chem. Commun., 1159; c) Dong G.X., Li J.S. and Chan T.H. (1995) J. Chem. Soc., Chem. Commun., 1725
Schick G., Jarosson T. and Rubin Y. (1999) Angew. Chem. Int. Ed. Engl. 38, 2360.
Arce M.J., Viado A.L., An Y.Z., Khan S.I. and Rubin Y. (1996) J. Am. Chem. Soc. 118, 3775.
Murata Y., Kato N. and Komatsu K. (2001) J. Org. Chem. 66, 7235.
Murata Y., Murata M. and Komatsu K. (2001) J. Org. Chem. 66, 8187.
As a recent review on C60 dimers, see: Segura J.L. and Martin N. (2000) Chem. Soc. Rev. 29, 13.
Inoue H., Yamaguchi H., Iwamatsu S., Uozaki T., Suzuki T., Akasaka T., Nagase S. and Murata S. (2001) Tetrahedron Lett. 42, 895.
For a recent review on o-quinodimethanes, see: Segura J.L. and Martin N. (1999) Chem. Rev. 99, 3199.
Fishwick C.W.G. and Jones D.W., in The Chemistry of Quinonoid Compounds (Eds., Patai S. and Rappoport Z.), John Wiley &; Sons Ltd.; 1988, vol. 2, 403–453.
Roth W.R., Biermann M., Dekker H., Jochems R., Mosselman C. and Hermann H. (1978) Chem. Ber. 111, 3892
Roth W.R. and Scholz B.P. (1981) Chem. Ber. 114, 3741.
Belik P., Gügel A., Spikermann J. and Müllen K. (1993) Angew. Chem. Int. Ed. Engl. 32, 78.
Tago T., Minowa T., Okada Y. and Nishimura J. (1993) Tetrahedron Lett. 34, 8461.
Gügel A., Kraus A., Spickermann J., Belik P. and Müllen K. (1994) Angew. Chem. Int. Ed. Engl. 33, 559.
Belik P., Gügel A., Kraus A., Spickermann J., Enkelmann V., Frank G. and Müllen K. (1993) Adv. Mater. 5, 854.
Zhang X. and Foote Ch. S. (1994) J. Org. Chem. 59, 5235.
Tomioka H. and Yamamoto K. (1995) J. Chem. Soc. Chem. Commun., 1961.
Tomioka H., Ichihashi M. and Yamamoto K. (1995) Tetrahedron Lett. 36, 5371.
Kraus A., Schenider M., Gügel A. and Müllen K. (1997) J. Mater. Chem. 7, 763.
Walter M., Gügel A., Spickermann J., Belik P., Kraus A. and Müllen K. (1996) Fullerenes Sci. & Tech., 101.
Puplovskis A., Kacens J. and Neilands O. (1997) Tetrahedron Lett. 38, 285.
Taki M., Takigami S., Watanabe Y., Nakamura Y. and Nishimura J. (1997) Polym. J. 29, 1020.
Pyo S., Shu L. and Echegoyen L. (1998) Tetrahedron Lett. 39, 7653.
Iyoda M., Sultana F., Sasaki S. and Butenschön H. (1995) Tetrahedron Lett. 36, 579.
Rubin Y., Khan S., Freedberg D.I. and Yeretzian C. (1993) J. Am. Chem. Soc. 115, 344.
Nakamura Y., Minowa T., Tobita S., Shizuka H. and Nishimura J. (1995) J. Chem. Soc. Perkin Trans. 2, 2351
Nakamura Y., Minowa T., Hayashida Y., Tobita S., Shizuka H. and Nishimura J. (1996) J. Chem. Soc. Faraday Trans. 92, 377
Nakamura Y., Taki M., Tobita S., Shizuka H., Yokoi H., Ishiguro K., Sawaki Y. and Nishimura J. (1999) J. Chem. Soc. Perkin Trans. 2, 127.
Isaacs L., Haldimann R.F. and Diederich F. (1994) Angew. Chem. Int. Ed. Engl. 33, 2339.
Taki M., Sugita S., Nakamura Y., Kasashima E., Yashima E., Okamoto Y. and Nishimura J. (1997) J. Am. Chem. Soc. 119, 926.
For recent reviews, see: a) Jensen A.W., Wilson S.R. and Schuster D.I. (1996) Bioorg. & Med. Chem. 4, 767; b) Da Ros, T. and Prato, M. (1999) Chem. Commun. 663.
Linsen T.G., Dürr K., Hanack M. and Hirsch A. (1995) J. Chem. Soc. Chem. Commun., 103.
Ishi-I T., Nakashima K. and Shinkai S. (1998) Chem. Commun., 1407.
Nakamura Y., Okawa K., Matsumoto M. and Nishimura J. (2000) Tetrahedron 56, 5429.
Ohno M., Koide N. and Eguchi S. (1995) Heterocyclic Commun. 1, 125.
Fernández-Paniagua U.M., Illescas B.M., Martin N. and Seoane C. (1996) J. Chem. Soc. Perkin Trans 1, 1077.
For a more general review of heterocyclic-containing [60]fullerene derivatives, see: Eguchi S., Ohno M., Kojima S., Koide N., Yashiro A., Shirakawa Y. and Ishida H. (1996) Fullerene Sci & Tech. 4, 303.
Arbogast J.W., Darmanyan A.P., Foote C.S., Rubin Y., Diederich F., Alvarez M.M., Anz S.J. and Whetten R.J. (1991) J. Phys. Chem. 95, 11
Wasiliewsky M.R., O’Neil M.P., Lykke K.R., Pellin M.J. and Gruen D.M. (1991) J. Am. Chem. Soc. 113, 2774
For a recent review on the photophysics and photochemistry of fullerene materials, see; Sun Y.-P., Marcel Dekker, New York, 1997, Vol. 1.
Trahanovsky W.S., Cassady T.J. and Woods T.L. (1981) J. Am. Chem. Soc. 103, 6691.
Ohno M., Koide N., Sato H. and Eguchi S. (1997) Tetrahedron 53, 9075.
Torres-Garcia G., Luftmann H. and Wolff C., Mattay J. (1997) J. Org. Chem. 62, 2752.
Fernández-Paniagua U.M., Illescas B., Martin N., Seoane C., de la Cruz P., de la Hoz A. and Langa F. (1997) J. Org. Chem. 62, 3705.
Guldi D.M., Torres-Garcia G. and Mattay J. (1998) J. Phys. Chem. 102, 9679.
Herrera A., Martinez R., Gonzalez B., Illescas B., Martin N. and Seoane C. (1997) Tetrahedron Lett. 38, 4873
Gonzalez B., Herrera A., Illescas B., Martin N., Martinez R., Moreno F., Sáncjez L. and Sanchez A. (1998) J. Org. Chem. 63, 6807
Tome A. C., Enes R., Cavaleiro J. and Elguero J. (1997) Tetrahedron Lett. 38, 2557.
For a recent review, see: Thilgen C., Herrmann A. and Diederich F. (1997) Angew. Chem. Int. Ed. Engl. 36, 2268.
Herrmann A., Diederich F., Thilgen C., ter Meer H.-U. and Müller W. H. (1994) Helv. Chim. Acta 77, 1689.
Seiler P., Herrmann A. and Diederich F. (1995) Helv. Chim. Acta 78, 344.
Hawkins J.M. and Meyer A. (1993) Science 260, 1918
Haddon R.C. and Scott L.T. (1986) Pure Appl. Chem. 58, 137
Haddon R.C. (1993) Science 261, 1545.
Arias F., Xie Q., Wu Y., Lu Q., Wilson S.R. and Echegoyen L. (1994) J. Am. Chem. Soc. 116, 6388
Allemand P.-M., Koch A., Wudl F., Rubin Y., Diederich F., Alvarez M.M., Anz S.J. and Whetten R.L. (1991) J. Am. Chem. Soc. 113, 1050
Haufler R.E., Conceiçao J., Chibante L.F.P., Chai Y., Byrne N.E., Flanagan S., Haley M.M., O’Brien S., Pan C., Xiao Z., Billups W.E., Ciufolini M.A., Hauge R.H., Margrave J.L., Wilson L.J., Curl R.F. and Smalley R.E. (1990) J. Phys. Chem. 94, 1050.
Williams R.M., Koeberg M., Lawson J.M., An Y.-Z., Rubin Y., Paddon-Row M.N. and Verhoeven J.W. (1996) J. Org. Chem. 61, 5055.
For a review, see: Martín N., Sánchez L., Illescas B. and Pérez I. (1998) Chem. Rev. 98, 2527.
Linssen T., Dürr K., Hanack M. and Hirsch A. (1995) J. Chem. Soc., Chem. Commun., 103
Dürr K., Fiedler S., Linssen T., Hirsch A. and Hanack M. (1997) Chem. Ver./Recueil 130, 1375.
For a review, see: Imahori H. and Sakata Y. (1997) Adv. Mater. 9, 537.
Imahori H., Hagiwara K., Akiyama T., Taniguchi S., Okada T. and Sakata Y. (1995) Chem. Lett., 265.
Imahori H., Hagiwara K., Aoki M., Akiyama T., Taniguchi S., Okada T., Shirakawa M. and Sakata Y. (1996) J. Am. Chem. Soc 118, 11771.
Illescas B.M., Martin N., Seoane C., Ortf E., Viruela P.M., Viruela R. and de la Hoz A. (1997) J. Org. Chem. 62, 7585.
Iyoda M., Sultana F., Sasaki S. and Yoshida M. (1994) J. Chem. Soc. Chem. Commun., 1929
Iyoda M., Sasaki S., Sultana F., Yoshida M., Kuwatani Y. and Nagase S. (1996) Tetrahedron Lett. 37, 7987.
Martín N., Sánchez L., Seoane C., Andreu R., Garín J. and Orduna J. (1996) Tetrahedron Lett. 37, 5979.
Prato M., Maggini M., Giacometti C., Scorrano G., Sandonà G. and Farnia G. (1996) Tetrahedron 52, 5221.
Boulle C., Rabreau J.M., Hudhomme P., Cariou M., Jubault M., Gorgues A., Orduna J. and Garin J. (1997) Tetrahderon Lett.38, 3909.
Llacay J., Veciana J., Vidal-Gancedo J., Bourdelande J.L., Gonzalez-Moreno R. and Rovira C. (1998) J. Org. Chem. 63, 5201.
Wudl F., Wobschall D. and Hufnagel E.J. (1972) J. Am. Chem. Soc. 94, 3372
For a recent review on TTF, see: Segura J.L. and Martin N. (2001) Angew. Chem. Int. Ed. 40, 1372.
Llacay J., Veciana J., Vidal-Gancedo J., Bourdelande J.L., Gonzalez-Moreno R. and Rovira C. (1998) J.Org. Chem. 63, 5201.
Boulle C., Cariou M., Bainville M., Gorgues A., Hudhomme P., Orduna J. and Garin J (1997) Tetrahedron Lett. 38, 81.
Llacay J., Mas M., Molins E., Veciana J. and Rovira C. (1997) Chem. Commun., 659.
Kreher D., Liu S.-G., Cariou M., Hudhomme P., Gorgues A., Mas M., Veciana J. and Rovira C. (2001) Tetrahedron Lett. 42, 3447.
The synthesis of a soluble C60-TTF-C60 system has been previously reported. See: Segura J.L., Priego E.M. Martin N., Luo Ch. and Guldi D.M. (2000) Org. Lett. 2, 4021.
Liu S.-G., Kreher D., Hudhomme P., Levillain E., Cariou M., Delaunay J., Gorgues A., Vidal-Gancedo J., Veciana J. and Rovira C. (2001) Tetrahedron Lett. 42, 3717.
Herranz M.A. and Martin N. (1999) Org. Lett. 1, 2005.
For a recent review on π-extended TTFs, see: Martin N. and Ortí E. “Quinonoid π-extended Tetrathiafulvalenes (TTFs)”, in Handbook of Advanced Electronic and Photonic Materials and Devices, Nalwa H.S. Ed. Vol. 3, Academic Press, 2001.
Martin N., Sánchez L. and Guldi D. (2000) Chem. Commun., 113.
Diels O. and Alder K. (1928) Ann.460, 98
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Martín, N., Segura, J.L., Wudl, F. (2002). New Concepts in Diels-Alder Cycloadditions to Fullerenes. In: Guldi, D.M., Martin, N. (eds) Fullerenes: From Synthesis to Optoelectronic Properties. Developments in Fullerene Science, vol 4. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9902-3_3
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