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Principles of Fullerene Reactivity

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Fullerenes and Related Structures

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 199))

Abstract

The fullerenes have been established as new and versatile building blocks in organic chemistry. A large number of fascinating fullerene derivatives, especially of the icosahedral buck-minsterfullerene C60, have been synthesized. The chemistry of C60 continues to be good for many surprises. However, based on present knowledge a series of reactivity principles can be deduced which makes derivatization of this all carbon cluster more and more predictable. In this article first the geometric and electronic properties of the parent molecule are analyzed. The bent structure of the carbon network C60 and the filling of its molecular orbital with 60 π-electrons dictate the chemical reactivity. A very important aspect that was introduced with the investigation of fullerene chemistry is the shape dependence of reactivity.

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References

  1. Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) Nature 318:162

    Article  CAS  Google Scholar 

  2. Krätschmer W, Lamb LD, Fostiropoulos K, Huffman DR (1990) Nature 347:354

    Article  Google Scholar 

  3. Hirsch A (1994) The chemistry of the fullerenes. Thieme, Stuttgart

    Google Scholar 

  4. Diederich F, Isaacs L, Philip D (1994) Chem Soc Rev 243

    Google Scholar 

  5. Hirsch A (1995) Synthesis 895

    Google Scholar 

  6. Diederich F, Thilgen C (1996) Science 271:317

    Article  CAS  Google Scholar 

  7. Rubin Y (1997) Chem Eur J 3:1009

    Article  CAS  Google Scholar 

  8. Hebard AF, Rosseinsky MJ, Haddon RC, Murphy DW, Glarum SH, Palstra TTM, Ramirez AP, Kortan AR (1991) Nature 350:600

    Article  CAS  Google Scholar 

  9. Holczer K, Klein O, Huang S-M, Kaner RB, Fu KJ, Whetten RL, Diederich F (1991) Science 252:1154

    CAS  Google Scholar 

  10. Hummelen JC, Prato M, Wudl F (1995) J Am Chem Soc 117:7003

    Article  CAS  Google Scholar 

  11. Murphy TA, Pawlik T, Weidinger A, Höhne M, Alcala R, Spaeth JM (1996) Phys Rev Lett 77:1075

    Article  CAS  Google Scholar 

  12. Mauser H, Hommes NvE, Clark T, Hirsch A, Pietzak B, Weidinger A, Dunsch L (1997) Angew Chem Int Ed Engl 36:2835

    Article  CAS  Google Scholar 

  13. Averdung J, Luftmann H, Schlachter I, Mattay J (1995) Tetrahedron 51:6977

    Article  CAS  Google Scholar 

  14. Lamparth I, Nuber B, Schick G, Skiebe A, Grösser T, Hirsch A (1995) Angew Chem 107:2473

    Article  Google Scholar 

  15. Lamparth I, Nuber B, Schick G, Skiebe A, Grösser T, Hirsch A (1995) Angew Chem Int Ed Engl 34:2257

    Article  CAS  Google Scholar 

  16. Hummelen JC, Knight B, Pavlovich J, Gonzalez R, Wudl F (1995) Science 269:1554

    Article  CAS  Google Scholar 

  17. Nuber B, Hirsch A (1996) J Chem Soc Chem Commun 1421

    Google Scholar 

  18. Sygula A, Rabideau PW (1994) J Chem Soc Chem Commun 2271

    Google Scholar 

  19. Djojo F, Hirsch A (1998) Chem Eur J 2:344

    Article  Google Scholar 

  20. Schmalz TG, Seitz WA, Klein DJ, Hite GE (1986) Chem Phys Lett 130:203

    Article  CAS  Google Scholar 

  21. Kroto HW (1987) Nature 329:529

    Article  CAS  Google Scholar 

  22. Beckhaus HD, Rüchardt C, Kao M, Diederich F, Foote CS (1992) Angew Chem 104:69

    Article  CAS  Google Scholar 

  23. Beckhaus HD, Rüchardt C, Kao M, Diederich F, Foote CS (1992) Angew Chem Int Ed Engl 31:63

    Article  Google Scholar 

  24. Haddon RC (1993) Science 261:1545

    Article  CAS  Google Scholar 

  25. Haddon RC (1986) J Am Chem Soc 108:2837

    Article  CAS  Google Scholar 

  26. Haddon RC (1987) J Am Chem Soc 109:1676

    Article  CAS  Google Scholar 

  27. Haddon RC (1988) Acc Chem Res 21:243

    Article  CAS  Google Scholar 

  28. Haddon RC (1990) J Am Chem Soc 112:3385

    Article  CAS  Google Scholar 

  29. Haddon RC (1992) Acc Chem Res 25:127

    Article  CAS  Google Scholar 

  30. Haddon RC, Brus LE, Raghavachari K (1986) Chem Phys Lett 125:459

    Article  CAS  Google Scholar 

  31. Haddon RC, Brus LE, Raghavachar K (1986) Chem Phys Lett 131:165

    Article  CAS  Google Scholar 

  32. Schulman M, Disch RL, Miller MA, Peck RC (1987) Chem Phys Lett 141:45

    Article  CAS  Google Scholar 

  33. Lüthi HP, Almöf J (1987) Chem Phys Lett 135:357

    Article  Google Scholar 

  34. Dunlap DI (1988) Int J Quantum Chem Symp 22:257

    Article  CAS  Google Scholar 

  35. Scuseria GE (1991) Chem Phys Lett 176:423

    Article  CAS  Google Scholar 

  36. Häser M, Almhöf J, Scuseria GE (1991) Chem Phys Lett 181:497

    Article  Google Scholar 

  37. Yannoni CS, Bernier PP, Bethune DS, Meijer G, Salem JR (1991) J Am Chem Soc 113:3190

    Article  CAS  Google Scholar 

  38. David WIF, Ibberson RM, Mathewman JC, Prassides K, Dennis TJS, Hare JP, Kroto HW, Taylor R, Walton DRM (1991) Nature 353:147

    Article  CAS  Google Scholar 

  39. Hedberg K, Hedberg L, Bethune DS, Brown CA, Dorn HC, Johnson RD, de Vries M (1991) Science 254:410

    Article  CAS  Google Scholar 

  40. Liu S, Lu YJ, Kappes MM, Ibers JA (1991) Nature 254:408

    CAS  Google Scholar 

  41. Andreoni W, Gygi F, Parinello M (1992) Phys Rev Lett 68:823

    Article  CAS  Google Scholar 

  42. Kohanoff J, Andreoni W, Parinello M (1992) Chem Phys Lett 198:472

    Article  CAS  Google Scholar 

  43. Stollhoff G (1991) Phys Rev B 44:10, 998

    Article  Google Scholar 

  44. Stollhoff G, Scherrer H (1995) Mater Sci Forum 191:81

    Article  CAS  Google Scholar 

  45. Dresselhaus MS, Dresselhaus G, Eklund PC (1995) Science of fullerenes and carbon nanotubes. Academic Press, New York

    Google Scholar 

  46. Xie Q, Perez-Cordero E, Echegoyen L (1992) J Am Chem Soc 114:3978

    Article  CAS  Google Scholar 

  47. Ohsawa Y, Saji T (1992) J Chem Soc Chem Commun 781

    Google Scholar 

  48. Fhou F, Jehoulet C, Bard AJ (1992) J Am Chem Soc 114:11, 004

    Google Scholar 

  49. Allemand P-M, Khemani KC, Koch A, Wudl F, Holczer K, Donovan S, Grüner G, Thompson JD (1991) Science 253:301

    Article  CAS  Google Scholar 

  50. Stephens PW, Cox D, Lauher JW, Mihaly L, Wiley JB, Allemand P-M, Hirsch A, Holczer K, Li Q, Thompson JD, Wudl F (1992) Nature355:331

    Article  CAS  Google Scholar 

  51. Bossard C, Rigaut S, Astruc D, Delville M-H, Felix G, Fevrier-Bouvier A, Amiall J, Flandrois S, Delhaes P (1993) J Chem Soc Chem Commun 333

    Google Scholar 

  52. Penicaud A, Hsu J, Reed C, Koch A, Khemani KC, Allemand P-M, Wudl F (1991) J Am Chem Soc 113:6699

    Article  Google Scholar 

  53. Xie Q, Arias F, Echegoyen L (1993) J Am Chem Soc 115:9818

    Article  CAS  Google Scholar 

  54. Haddon RC (1995) Nature 378:249

    Article  CAS  Google Scholar 

  55. Elser V, Haddon RC (1987) Nature 325:1987

    Article  Google Scholar 

  56. Bühl M (1998) Chem Eur J 4:734

    Article  Google Scholar 

  57. Saunders M, Jiminez-Vazquez HA, Cross RJ, Mroczkowski S, Freedberg DI, Anet FAL (1994) Nature 367:256

    Article  CAS  Google Scholar 

  58. Saunders M, Cross RJ, Jiminez-Vazquez HA, Shimshi R, Khong A (1996) Science 271:1693

    Article  CAS  Google Scholar 

  59. Wudl F, Hirsch A, Khemani KC, Suzuki T, Allemand P-M, Koch A, Eckert H, Srdanov HG, Webb H (1992) In: Hammond GS, Kuck VJ (eds) Fullerenes. American Chemical Society Symposium Series 481:161

    Google Scholar 

  60. Hirsch A, Li Q, Wudl F (1991) Angew Chem 103:1339

    Article  CAS  Google Scholar 

  61. Hirsch A, Li Q, Wudl F (1991) Angew Chem Int Ed Engl 30:1309

    Article  Google Scholar 

  62. Hirsch A, Soi A, Karfunkel HR (1992) Angew Chem 104:808

    Article  CAS  Google Scholar 

  63. Hirsch A, Soi A, Karfunkel HR (1992) Angew Chem Int Ed Engl 31:766

    Article  Google Scholar 

  64. Hirsch A, Grösser T, Skiebe A, Soi A (1993) Chem Ber 126:1061

    Article  CAS  Google Scholar 

  65. Fagan PJ, Krusic PJ, Evans DH, Lerke SA, Johnston E (1992) J Am Chem Soc 114:9697

    Article  CAS  Google Scholar 

  66. Bingel C (1993) Chem Ber 126:1957

    Article  CAS  Google Scholar 

  67. Kampe K-D, Egger N, Vogel M (1993) Angew Chem 105:1203

    Article  CAS  Google Scholar 

  68. Schick G, Kampe K-D, Hirsch A (1995) J Chem Soc, Chem Commun 2023

    Google Scholar 

  69. Camps X, Hirsch A (1997) J Chem Soc, Perkin Trans 1 1595

    Article  Google Scholar 

  70. Yamogo S, Yanagawa M, Nakamura E (1994) J Chem Soc Chem Commun 2093

    Google Scholar 

  71. Davey SN, Leigh DA, Moody AE, Tetler LW, Wade FA (1994) J Chem Soc Chem Commun. 397

    Google Scholar 

  72. Nagashima H, Terasaki H, Kimura E, Nakajima K, Itoh K (1994) J Org Chem 59:1246

    Article  CAS  Google Scholar 

  73. Keshawarz K M, Knight B, Srdanov G, Wudl F (1995) J Am Chem Soc 117:11, 371

    Google Scholar 

  74. Timmermann P, Witschel LE, Diederich F, Boudon C, Gisselbrecht J-P, Gross M (1996) Helv Chim Acta 79:6

    Article  Google Scholar 

  75. Osterodt J, Vögtle F (1996) Chem Commun 547

    Google Scholar 

  76. Mikami K, Matsumoto S, Ishida A, Takamuku S, Suenobu T, Fukuzumi S (1995) J Am Chem Soc 117:11, 134

    Article  Google Scholar 

  77. Murata Y, Komatsu K, Wan TSM (1996) Tetrahedron Lett 37:7061

    Article  CAS  Google Scholar 

  78. Nagashima H, Terasaki H, Saito Y, Jinno K, Itoh K (1995) J Org Chem 60:4966

    Article  CAS  Google Scholar 

  79. Murata Y, Shiro M, Komatsu K (1997) J Am Chem Soc 119:8117

    Article  CAS  Google Scholar 

  80. Sawamura M, Iikura H, Nakamura E (1996) J Am Chem Soc 118:12, 850

    Google Scholar 

  81. Okamura H, Murata Y, Minoda M, Komatsu K, Miyamoto T, Wan TSM (1996) J Org Chem 61:8500

    Article  CAS  Google Scholar 

  82. Paulus EF, Bingel C (1995) Acta Cryst C 51:143

    Article  Google Scholar 

  83. Kampe K-D, Egger N (1995) Liebigs Ann 115

    Google Scholar 

  84. Komatsu K, Murata Y, Takimoto N, Mori S, Sugita N, Wan TSM (1994) J Org Chem 59:6101

    Article  CAS  Google Scholar 

  85. Murata Y, Motoyama K, Komatsu K, Wan TSM (1996) Tetrahedron 52:5077

    Article  CAS  Google Scholar 

  86. Murata Y, Komatsu K, Wan TSM (1996) Tetrahedron Lett 37:7061

    Article  CAS  Google Scholar 

  87. Komatsu K, Takimoto N, Murata Y, Wan TSM, Wong T (1996) Tetrahedron Lett 37:6153

    Article  CAS  Google Scholar 

  88. Okamura H, Minoda M, Komatsu K, Miyamoto T (1997) Macromol Chem Phys 198:777

    Article  CAS  Google Scholar 

  89. Wang G-W, Komatsu K, Murata Y, Shiro M (1997) Nature 387:583

    Article  CAS  Google Scholar 

  90. Tanaka T, Kitagawa T, Komatsu K, Takeuchi K (1997) J Am Chem Soc 119:9313

    Article  CAS  Google Scholar 

  91. Kitagawa T, Tanaka T, Takata Y, Takeuchi K (1995) J Org Chem 60:1490

    Article  CAS  Google Scholar 

  92. Ganapathi PS, Friedmann SH, Kenyon GL, Rubin Y (1995) J Org Chem 60:2954

    Article  CAS  Google Scholar 

  93. Kusukawa T, Ando W (1996) Angew Chem 108:1416

    Article  Google Scholar 

  94. Morton JR, Preston KF, Krusic PJ, Hill SA, Wasserman E (1992) J Phys Chem 96:3576

    Article  CAS  Google Scholar 

  95. Morton JR, Preston KF, Krusic PJ, Hill SA, Wasserman E (1992) J Am Chem Soc 114:5454

    Article  CAS  Google Scholar 

  96. Morton JR, Preston KF, Krusic PJ, Wasserman E (1992) J Chem Soc, Perk Trans 2, 1425

    Article  Google Scholar 

  97. Krusic PJ, Roe DC, Johnston E, Morton JR, Preston KF (1993) J Phys Chem 97:1736

    Article  CAS  Google Scholar 

  98. Morton JR, Preston KF, Krusic PJ, Knight LB (1993) J Chem Phys Lett 204:481

    Article  CAS  Google Scholar 

  99. Keizer PN, Morton JR, Preston KF (1992) J Chem Soc Chem Commun 1259

    Google Scholar 

  100. Johnson CSJr (1964) J Chem Phys 41:3277

    Article  CAS  Google Scholar 

  101. Krusic P, Meakin P, Jesson JP (1971) J Phys Chem 75:3438

    Article  CAS  Google Scholar 

  102. Fagan PJ, Krusic PJ, Evans DH, Lerke SA, Johnston E (1992) J Am Chem Soc 114:9697

    Article  CAS  Google Scholar 

  103. Krusic PJ, Wasserman E, Parkinson BA, Malone B, Holler ER, Keizer PN, Morton JR, Preston KF (1991) J Am Chem Soc 113:6274

    Article  CAS  Google Scholar 

  104. Krusic PJ, Wasserman E, Keizer PN, Morton JM, Preston KF (1991) Science 254:1183

    Article  CAS  Google Scholar 

  105. Fagan PJ, Krusic PJ, McEven CN, Lazar L, Holmes Parker D, Herron N, Wasserman E (1993) Science 262:404

    Article  CAS  Google Scholar 

  106. Loy DA, Assink R (1992) J Am Chem Soc 114:3977

    Article  CAS  Google Scholar 

  107. Skiebe A, Hirsch A, Klos H, Gotschy B (1994) Chem Phys Lett 220:138

    Article  CAS  Google Scholar 

  108. Djojo F, Herzog A, Lamparth I, Hampel F, Hirsch A (1996) Chem Eur J 2:1537

    Article  CAS  Google Scholar 

  109. Matsuzawa N, Dixon DA, Fukunaga T (1992) J Phys Chem 96:7594

    Article  CAS  Google Scholar 

  110. Tsuda M, Ishida T, Nogami T, Kurono S, Ohashi M (1993) J Chem Soc, Chem Commun 1296

    Google Scholar 

  111. Schlueter JA, Seaman JM, Taha S, Cohen H, Lykke KR, Wang HH, Williams JM (1993) J Chem Soc Chem Commun 972

    Google Scholar 

  112. Komatsu K, Murata Y, Sugita N, Takeuchi K, Wan TSM (1993) Tetrahedron Lett 34:8473

    Article  CAS  Google Scholar 

  113. Lamparth I, Maichle-Mössmer C, Hirsch A (1995) Angew Chem 107:1755

    Article  Google Scholar 

  114. Lamparth I, Maichle-Mössmer C, Hirsch A (1995) Angew Chem Int Ed Engl 34:1607

    Article  CAS  Google Scholar 

  115. Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H-B (1996) Angew Chem 108:1294

    Article  Google Scholar 

  116. Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H-B (1996) Angew Chem Int Ed Engl 35:1203

    Google Scholar 

  117. Rotello VM, Howard JB, Yadev T, Conn MM, Viani E, Giovane LM, Lafleur AL (1993) Tetrahedron Lett 34:1561

    Article  CAS  Google Scholar 

  118. Gügel A (1993) Doctoral Thesis, Max-Plank Institut, Mainz

    Google Scholar 

  119. Tsuda M, Ishida T, Nogami T, Kurono S, Ohashi M (1992) Chem Lett 2333

    Google Scholar 

  120. Hoke SHII, Molstad J, Dilattato D, Jay MJ, Carlson D, Kahr B, Cooks RG (1992) J Org Chem 57:5069

    Article  CAS  Google Scholar 

  121. Prato M, Lucchini V, Maggini M, Stimpfl E, Scorrano G, Eiermann M, Suzuki T, Wudl F (1993) J Am Chem Soc 115:8479

    Article  CAS  Google Scholar 

  122. Prato M, Li Q, Wudl F, Lucchini V (1993) J Am Chem Soc115:1148

    Article  CAS  Google Scholar 

  123. Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Rankin DWH (1994) J Chem Soc Chem Commun 1365

    Google Scholar 

  124. Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Taylor AT (1994) Tetrahedron Lett 35:9067

    Article  CAS  Google Scholar 

  125. Ishida T, Tanaka K, Nogami T (1994) Chem Lett 561

    Google Scholar 

  126. Hawker CJ, Wooley KL, Frechet JMJ (1994) J Chem Soc Chem Commun 925

    Google Scholar 

  127. Yan M, Cai SX, Keana JFW (1994) J Org Chem 59:5951

    Article  CAS  Google Scholar 

  128. Averdung J, Luftmann H, Mattay J, Claus KU, Abraham W (1995) Tetrahedron Lett 36:2957

    Article  CAS  Google Scholar 

  129. Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Parkinson JAS, Rankin DWH, Taylor AT (1995) J Chem Soc Chem Commun 887

    Google Scholar 

  130. Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Taylor AT (1995) J Chem Soc Chem Commun 88

    Google Scholar 

  131. Schick G, Grösser T, Hirsch A (1995) J Chem Soc Chem Commun 2289

    Google Scholar 

  132. Schick G, Hirsch A, Mauser H, Clark T (1996) Chem Eur J 2:935

    Article  CAS  Google Scholar 

  133. Grösser T, Prato M, Lucchini V, Hirsch A, Wudl F (1995) Angew Chem 107:1462

    Article  Google Scholar 

  134. Grösser T, Prato M, Lucchini V, Hirsch A, Wudl F (1995) Angew Chem Int Ed Engl 34:1343

    Article  Google Scholar 

  135. Schick G, Hirsch A (1998) Tetrahedron 54:4283

    Article  CAS  Google Scholar 

  136. Haldiman RF, Klärner F-G, Diederich F (1997) J Chem Soc Chem Commun 237

    Google Scholar 

  137. Shen CF-F, Yu H-H, Juo CG, Chien KM, Her G-R, Luh T-Y (1997) Chemistry Eur J 3:744

    Article  CAS  Google Scholar 

  138. Wudl F (1992) Acc Chem Res 25:157

    Article  CAS  Google Scholar 

  139. Diederich F, Isaacs L, Philp D (1994) Chem Soc Rev 243

    Google Scholar 

  140. Janssen RAJ, Hummelen JC, Wudl F (1995) J Am Chem Soc 117:544

    Article  CAS  Google Scholar 

  141. Isaacs L, Wehrsig A, Diederich F (1993) Helv Chim Acta 76:1231

    Article  CAS  Google Scholar 

  142. Smith ABIII, Strongin RM, Brard L, Furst GT, Romanow WJ, Owens KG, King RC (1993) J Am Chem Soc 115:5829

    Article  CAS  Google Scholar 

  143. Smith ABIII, Strongin RM, Brard L, Furst GT, Romanow WJ, Owens KG, Goldschmidt RJ, King RC (1995) J Am Chem Soc 117:5492

    Article  CAS  Google Scholar 

  144. Saunders M (1991) Science 253:330

    Article  CAS  Google Scholar 

  145. Banks MR, Dale MJ, Gosney I, Hodgson PKG, Jennings RCK, Jones AC, Lecoultre J, Langridge-Smith PRR, Maier JP, Scrivens JH, Smith MJC, Smyth CJ, Taylor AT, Thorburn P, Webster AS (1993) J Chem Soc Chem Commun 1149

    Google Scholar 

  146. Rüchhardt C, Gerst M, Ebenhoch J, Beckhaus H-D, Campbell EEB, Tellgmann R, Schwarz H, Weiske T, Pitter S (1993) Angew Chem 105:609 (1993) Angew Chem Int EdEngl 32: 584

    Article  Google Scholar 

  147. Vassallo AM, Wilson MA, Attalla MI (1988) Energy Fuels 2:539

    Article  CAS  Google Scholar 

  148. Attalla MI, Wilson MA, Quezada RA, Vassallo AM (1989) Energy Fuels 3:59

    Article  CAS  Google Scholar 

  149. Attalla MI, Vassallo AM, Tattam BN, Hanna JV (1993) J Phys Chem 97:6329

    Article  CAS  Google Scholar 

  150. Henderson CC, Cahill PA (1993) Science 259:1885

    Article  CAS  Google Scholar 

  151. Ballenweg S, Gleiter R, Krätschmer W (1993) Tetrahedron Lett 34:3737

    Article  CAS  Google Scholar 

  152. Guarr TF, Meier MS, Vance VK, Clayton M (1993) J Am Chem Soc 115:9862

    Article  CAS  Google Scholar 

  153. Henderson CC, Assink RA, Cahill PA (1994) Angew Chem 106:803

    Article  CAS  Google Scholar 

  154. Henderson CC, Assink RA, Cahill PA (1994) Angew Chem Int Ed Engl 33:786

    Article  Google Scholar 

  155. Meier MS, Weedon BR, Spielmann HP (1996) J Am Chem Soc 118:11, 682

    Article  Google Scholar 

  156. Fagan PJ, Calabrese JC, Malone B (1992) In: Hammond GS, Kuck VS (eds) Fullerenes. ACS Symosium Series 481, Am Chem Soc, Washington DC, p 177

    Google Scholar 

  157. Balch AL, Catalano VJ, Lee JW (1991) Inorg Chem 30:3990

    Google Scholar 

  158. Balch AL, Catalano VJ, Lee JW, Olmstead MM (1992) J Am Chem Soc 114:5455

    Article  CAS  Google Scholar 

  159. Balch AL, Lee JW, Noll BC, Olmstead MM (1992) J Am Chem Soc 114:10,984

    Google Scholar 

  160. Balch AL, Catalano VJ, Lee JW, Olmstead MM, Parkin SR (1991) J Am Chem Soc 113:8953

    Article  CAS  Google Scholar 

  161. Koefod RS, Hudgens MF, Shapley JR (1991) J Am Chem Soc 113:8957

    Article  CAS  Google Scholar 

  162. Rasinkangas M, Pakkanen TT, Pakkanen TA, Ahlgren M, Rouvinen J (1993) J Am Chem Soc 115:4901

    Article  CAS  Google Scholar 

  163. Yagupsky G, Brown CK, Wilkinson GJ (1970) J Chem Soc A 1392

    Google Scholar 

  164. Diederich F, Ettl R, Rubin Y, Whetten RL, Beck R, Alvarez M, Anz S, Sehsharma D, Wudl F, Khemani KC, Koch A (1991) Science 252:548

    Article  CAS  Google Scholar 

  165. Wood JM, Kahr B, Hoke SHII, Dejarme L, Cooks RG, Ben-Amotz D (1991) J Am Chem Soc 113:5907

    Article  CAS  Google Scholar 

  166. Thorp HH, Karlsbeck WA (1991) J Electroanal Chem 314:363

    Article  Google Scholar 

  167. Taylor R, Parsons JP, Avent AG, Rannard SP, Dennis TJ, Hare JP, Kroto HW, Walton DRM (1991) Nature 351:277

    Article  CAS  Google Scholar 

  168. Creegan KM, Robbins JL, Robbins WK, Millar JM, Sherwood RD, Tindall PJ, Cox DM, Smith ABIII, McCauley JPJr, Jones DR, Gallagher RT (1992) J Am Chem Soc 114:1103

    Article  CAS  Google Scholar 

  169. Vassalo AM, Pang LSK, Coke-Clarke PA, Wilson MA (1991) J Am Chem Soc 113:7820

    Article  Google Scholar 

  170. Elemes Y, Silverman SK, Sheu C, Kao M, Foote CS, Alvarez MM, Whetten RL (1992) Angew Chem 104:364

    Article  CAS  Google Scholar 

  171. Elemes Y, Silverman SK, Sheu C, Kao M, Foote CS, Alvarez MM, Whetten RL (1992) Angew Chem Int Ed Engl 31:351

    Article  Google Scholar 

  172. Cataldo F, Ori O (1995) Polymer Degradation and Stability 48:291

    Article  CAS  Google Scholar 

  173. Hawkins JM, Lewis TA, Loren SD, Meyer A, Heath LR, Shibato Y, Saykally RJ (1990) J Org Chem 55:6250

    Article  CAS  Google Scholar 

  174. Hawkins JM, Meyer A, Lewis TA, Loren S, Hollander FJ (1991) Science 252:312

    Article  CAS  Google Scholar 

  175. Hawkins JM, Loren S, Meyer A, Nunlist R (1991) J Am Chem Soc 113:7770

    Article  CAS  Google Scholar 

  176. Hawkins JM (1992) Acc Chem Res 25:150

    Article  CAS  Google Scholar 

  177. Hawkins JM, Meyer A, Lewis TA, Bunz U, Nunlist R, Ball GE, Ebbesen TW, Tanigaki K (1992) J Am Chem Soc 114:7954

    Article  CAS  Google Scholar 

  178. Holloway JH, Hope EG, Taylor R, Langley GL, Advent AG, Dennis TJ, Hare JH, Kroto HW, Walton DRM (1991) J Chem Soc Chem Commun 966

    Google Scholar 

  179. Selig H, Lifshitz C, Peres T, Fischer JE, McGhie AR, Romanov WJ, McCauley JPJr, Smith AB III (1991) J Am Chem Soc 113:5475

    Article  CAS  Google Scholar 

  180. Kniaz K, Fischer JE, Selig H, Vaughan GBM, Romanov WJ, Cox D, Chowdhury K, McCauley JP, Strongin RM, Smith AB III (1993) J Am Chem Soc 115:6060

    Article  CAS  Google Scholar 

  181. Gakh AA, Tuinman AA, Adcock JL, Sachleben RA, Compton RN (1994) J Am Chem Soc 116:819

    Article  CAS  Google Scholar 

  182. Boltalina OV, Borschevskii AY, Sidorov LN, Street JM, Taylor R (1996) Chem Commun 529

    Google Scholar 

  183. Boltalina OV, Markov VY, Taylor R, Waugh MP (1996) Chem Commun 2549

    Google Scholar 

  184. Tuinman AA, Gakh AA, Adcock JL, Compton RN (1993) J Am Chem Soc 115:5885

    Article  CAS  Google Scholar 

  185. Olah GA, Bucsi I, Lambert C, Aniszfeld R, Trivedi NJ, Sensharma DK, Prakash GKS (1991) J Am Chem Soc 133:9385

    Article  Google Scholar 

  186. Tebbe FN, Becker JY, Chase DB, Firment LE, Holler ER, Malone BS, Krusic PJ, Wasserman E (1991) J Am Chem Soc 113:9900

    Article  CAS  Google Scholar 

  187. Birkett PR, Avent AG, Darwish AD, Kroto HW, Taylor R, Walton DRM (1993) J Chem Soc Chem Commun 1230

    Google Scholar 

  188. Tebbe FN, Harlow RL, Chase DB, Thorn DL, Campbell GCJr, Calabrese JC, Herron N, Young RJ, Wasserman E (1992) Science 256:822

    Article  CAS  Google Scholar 

  189. Birkett PR, Hitchcock PB, Kroto HW, Taylor R, Walton DRM (1992) Nature 357:479

    Article  CAS  Google Scholar 

  190. Birkett PR, Avent AG, Darwisch AD, Kroto HW, Taylor R, Walton DRM (1993) J Chem Soc Chem Commun 1230

    Google Scholar 

  191. Taylor R (1995) The chemistry of fullerenes. World Scientific, Singapore

    Google Scholar 

  192. Miller GP (1992) Mat Res Soc Symp Proc 247:293

    CAS  Google Scholar 

  193. Thoman H, Bernardo M, Miller GP (1992) J Am Chem Soc 114:6593

    Article  Google Scholar 

  194. Chiang LY, Swirczewski JW, Hsu CS, Chowdhury DK, Cameron S, Cressgan K (1992) J Chem Soc Chem Commun 1791

    Google Scholar 

  195. Chiang LY, Upasani RB, Swirczewski JW, Soled S (1993) J Am Chem Soc 115:5453

    Article  CAS  Google Scholar 

  196. Olah GA, Bucsi I, Lambert C, Aniszfeld R, Trivedi NJ, Sensharma DK, Prakash GK (1991) J Am Chem Soc 113:9387

    Article  CAS  Google Scholar 

  197. Taylor R, Langley GL, Meidine MF, Parsons JP, Abdul-Sada AK, Dennis TJ, Hare JP, Kroto HW, Walton DRM (1992) J Chem Soc Chem Commun 667

    Google Scholar 

  198. Olah GA personal communication

    Google Scholar 

  199. Hawkins JM, Meyer A, Lewis TA, Bunz U, Nunlist R, Ball GE, Ebbesen T, Tanigaki K (1992) J Am Chem Soc 114:7954

    Article  CAS  Google Scholar 

  200. Hawkins JM, Meyer A, Nambu M (1993) J Am Chem Soc 115:9844

    Article  CAS  Google Scholar 

  201. Hirsch A, Lamparth I, Karfunkel HR (1994) Angew Chem 106:453

    Article  CAS  Google Scholar 

  202. Hirsch A, Lamparth I, Karfunkel HR (1994) Angew Chem Int Ed Engl 33:437

    Article  Google Scholar 

  203. Hirsch A, Lamparth I, Grösser T, Karfunkel HR (1994) J Am Chem Soc 116:9385

    Article  CAS  Google Scholar 

  204. Avent AG, Darwish AD, Heimbach DK, Kroto HW, Meidine MF, Parsons JP, Remars C, Roers R, Ohashi O, Taylor R, Walton DRM (1994) J Chem Soc, Perkin Trans 2 15

    Google Scholar 

  205. Henderson CC, Assink RA, Cahill PA (1994) Angew Chem 106:803

    Article  CAS  Google Scholar 

  206. Henderson CC, Assink RA, Cahill PA (1994) Angew Chem Int Ed Engl 33:786

    Article  Google Scholar 

  207. Hamano T, Mashino T, Hirobe M (1995) J Chem Soc Chem Commun 1537

    Google Scholar 

  208. Cardullo F, Isaacs L, Diederich F, Gisselbrecht J-P, Boudon C, Gross M (1996) J. Chem Soc Chem Commun 797

    Google Scholar 

  209. Kräutler B, Maynollo J (1995) Angew Chem 107:69

    Article  Google Scholar 

  210. Kräutler B, Maynollo J (1995) Angew Chem Int Ed Engl 34:87

    Article  Google Scholar 

  211. Fagan PJ, Calabrese JC, Malone B (1991) J Am Chem Soc 113:9408

    Article  CAS  Google Scholar 

  212. Isaacs L, Haldimann RF, Diederich F (1994) Angew Chem 106:2435

    Article  Google Scholar 

  213. Isaacs L, Haldimann RF, Diederich F (1994) Angew Chem Int Ed Engl33:2434

    Article  Google Scholar 

  214. Isaacs L, Haldimann RF, Diederich F (1995) Angew Chem 107:1636

    Article  Google Scholar 

  215. Isaacs L, Haldimann RF, Diederich F (1995) Angew Chem Int Ed Engl 34:1466

    Article  CAS  Google Scholar 

  216. Diederich F, Thilgen C, Herrmann A (1996) Nachr Chem Tech Lab 44:9

    CAS  Google Scholar 

  217. Thilgen C, Herrmann A, Diederich F (1997) Helv Chem Acta 80:183

    Article  CAS  Google Scholar 

  218. Lamparth I, Herzog A, Hirsch A (1996) Tetrahedron 52:5065

    Article  CAS  Google Scholar 

  219. Camps X, Schönberger H, Hirsch A (1997) Chem Eur J 3:561

    Article  CAS  Google Scholar 

  220. Hirsch A, Lamparth I, Schick G (1996) Liebigs Ann 1725

    Google Scholar 

  221. Anderson HL, Boudon C, Diederich F, Gisselbrecht J-P, Gross M, Seiler P (1994) Angew Chem 106:1691

    Article  CAS  Google Scholar 

  222. Anderson HL, Boudon C, Diederich F, Gisselbrecht J-P, Gross M, Seiler P (1994) Angew Chem Int Ed Engl 33:1628

    Article  Google Scholar 

  223. Arce M-J, Viado AL, Khan S, Rubin Y (1996) Organometallics (in press)

    Google Scholar 

  224. Reuther U, Hirsch A (1998) J Chem Soc Chem Comm 1401

    Google Scholar 

  225. Bethune DS, Johnson DR, Salem JR, de Vries MS, Yannoni CS (1993) Nature 366:123

    Article  CAS  Google Scholar 

  226. Tellgmann R, Krawez N, Lin SH, Hertel IV, Campbell EFB (1996) Nature 382:407

    Article  CAS  Google Scholar 

  227. Knapp C, Dinse K-P, Pietzak B, Waiblinger M, Weidinger A (1997) Chem Phys Lett 272:433

    Article  CAS  Google Scholar 

  228. Mauser H, Hommes NvE, Clark T, Hirsch A, Pietzak B, Weidinger A, Dunsch L (1997) Angew Chem 109:2858

    Article  Google Scholar 

  229. Mauser H, Hommes NvE, Clark T, Hirsch A, Pietzak B, Weidinger A, Dunsch L (1997) Angew Chem Int Ed Engl 36:2835

    Article  CAS  Google Scholar 

  230. Pietzak B, Waiblinger M, Murphy TA, Weidinger A, Höhne M, Dietel E, Hirsch A (1997) Chem Phys Lett 279:259

    Article  CAS  Google Scholar 

  231. Mauser H, Hirsch A, Hommes NvE, Clark T (1997) J Mol Model 3:415

    Article  CAS  Google Scholar 

  232. Ebbesen W (1994) In: Kuzmany H, Fink J, Mehring M, Roth S (eds.) Progress in fullerene research. World Scientific, Singapore, p 116

    Google Scholar 

  233. Hirsch A, Mauser H, Clark T (1997) In: Kuzmany H, Fink J, Mehring M, Roth S (eds.) Molecular nanostructures. World Scientific Publishing, p 55

    Google Scholar 

  234. Seiders TJ, Beldridge KK, O’Connor JM, Siegel JS (1997) J Am Chem Soc 119:4781

    Article  CAS  Google Scholar 

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Hirsch, A. (1999). Principles of Fullerene Reactivity. In: Hirsch, A. (eds) Fullerenes and Related Structures. Topics in Current Chemistry, vol 199. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68117-5_1

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