Synthesis of heterocycles by transition metals-catalyzed cyclo-carbonylation reactions

Current Organic Chemistry

Volumn 10, Issue 12, 2006, Pages 1397-1421

  Vasapollo, Giuseppe ^a   Mele, Giuseppe ^a  

^a UNIVERSITY OF SALENTO   (Italy)

Author keywords

Building blocks; Lactones; Natural Non Steroidic Compounds; Palladium complexes; Pauson Khand type reaction; Resorcinol derivative

Indexed keywords

15 CYCLOHEXYL 15 HYDROXY 2',9ALPHA METHANO 4,5,6,16,17,18,19,20 OCTANOR 3 OXA 3,7 (1,3 INTERPHENYLENE)PROSTANOIC ACID; 2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; ALPHA METHYLENE LACTONE; ANTIBIOTIC AGENT; ANTIULCER AGENT; AZIRIDINE DERIVATIVE; BETA LACTAM DERIVATIVE; COBALT COMPLEX; FULLERENE DERIVATIVE; FULLEROPYRROLIDINE DERIVATIVE; FURAN DERIVATIVE; FURANONE DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; GAMMA LACTONE DERIVATIVE; HETEROCYCLIC COMPOUND; IRIDIUM; LACTAM DERIVATIVE; LACTONE DERIVATIVE; METAL COMPLEX; NICKEL COMPLEX; PALLADIUM COMPLEX; PHTHALOCYANINE DERIVATIVE; PLATINUM COMPLEX; PYRROLIZIDINE DERIVATIVE; RHODIUM COMPLEX; RUTHENIUM; STEROID; TRANSITION ELEMENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALLYLATION; CARBONYLATION; CATALYSIS; DRUG ISOLATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ISOMERIZATION; LACTONIZATION; NONHUMAN; POLYMERIZATION; QUANTITATIVE ANALYSIS; REVIEW; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 33747183061     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206778018276     Document Type: Review

References (177)

1. (a) Schore, N. E. Chem. Rev., 1988, 88, 1081.
2. (b) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct synthesis of carbonyl compounds. Plenum Press: New York 1991.
3. (c) Trost, B. M.; Fleming, I., Comprehensive Organic Synthesis Eds. Pergamon Press: New York, 1991.
4. (d) Alper, H. Aldrichimia. Acta, 1991, 24, 3.
5. (e) Hosakawa, T.; Murahashi, S. I. Heterocycles, 1992, 33, 1079.
6. (f) Parshall, G. W.; Ittel, S. D. "Homogeneous Catalysis", Wiley, New York 1993.
7. (g) Masters, C. "Homogeneous Transition Metal Catalysis", Wiley, New York 1993.
8. (h) Negishi, E. T.; Coperet, C.; Ma, S.; Lion, S.Y.; Liu, F. Chem. Rev., 1996, 96, 365.
9. (i) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev., 1996, 96, 635.
10. (j) Ungvary, F. Coord. Chem. Rev., 1998, 170, 245.
11. (k) El Ali, B.; Alper, H. Synlett, 2000, 161.
12. (l) Vasapollo, G.; Mele G. "Targets in Heterocyclic Systems" Italian Society of Chemistry, Rome 2002, 6, 197.
13. (m) Vizer, S. A.; Yerzhanov, K. B.; Al Aziz Al Quntarb, A.; Dembitsky, V. M. Tetrahedron, 2004, 60, 5499.
14. (a) Nakanishi, K.; Goto, T.; Ito, S. Natural Product Chemistry; Kodansya: Tokyo, 1974; vols. 1-3.
15. (b) Dictionary of Natural Products, 1st ed.; Buckingam, J., Ed. Chapman & Hall: New York. 1994.
16. (c) Rao, Y. S. Chem. Rev., 1976, 76, 5.
17. (d) Barton, D.; Nakanishi, K.; Meth-Cohn, O. In Comprehensive Natural Products Chemistry; Elsevier Science Ltd.: Oxford, 1999; Vol. 8, pp 378-385.
18. (e) Rao, G. V.; Cain, R. B. J. Chem. Soc., Perkin Trans. 1, 1996, 2111.
19. (f) Handa, S. Tetrahedron Asymmetry, 1996, 7, 1281.
20. (g) Knight, D. W. Contemp. Org. Synth., 1994, 1, 287.
21. (a) Raphael, R. A.; Ravenscroft, P. J. Chem. Soc., Perkin Trans., I 1988, 7, 1823.
22. (b) Dueholm, K. L.; Pederson, L. B. Synthesis, 1992, 1.
23. (c) Robertson, D. W.; Krushinski, J. H.; Utterback, B. G.; Kauffman, R. F. J. Med. Chem., 1989, 32, 1476.
24. (d) Bjeldanes, L. F.; Kim, I. S. J. Org. Chem., 1977, 42, 2333.
25. (e) Weidner-Wells M. A.; Decamp, A.; Mazzocchi, P. H. J. Org. Chem., 1989, 54, 5746.
26. (a) Al-Alzemi, T. F.; Kondaveti, L.; Bisht, K. S. Macromolecules, 2002, 35, 3380.
27. (b) Trollasas, M.; Hedrick, J. L.; Mecerreyes, D.; Dubois, P.; Jerome, R.; Ihre, H.; Hult, A. Macromolecules, 1998, 3,1 2756.
28. (a) da Silva, R.; de Souza, G. H. B.; Da Silva, A. A.; de Souza, V. A.; Pereira, A. C.; Royo, V. D.; Silva, M. L. A. E.; Donate, P. M.; Araujo, A. L. S. D.; Carvalho J. C. T.; Bastos J. K. Bioorg. Med. Chem. Lett. 2005, 15, 1033.
29. (b) Asakawa, Y.; Toyota, M.; Nagashima, F.; Hashimoto, T.; El Hassane, L. Heterocycles, 2001, 54, 1057.
30. (c) Miyazawa, M.; Shimabayashi, H.; Hayashi, S.; Hashimoto, S.; Nakamura, S.; Kosaka, H.; Kameoka, H. J. Agric. Food Chem. 2000, 48, 5406.
31. (a) Miranda, P. O.; Estevez, F.; Quintana, J.; Garcia, C. I.; Brouard, I; Padron, J. I.; Pivel, J. P.; Bermejo, J. J. Med. Chem. 2004, 47, 292.
32. (b) Mikell, J. R.; Schaneberg, B. T.; Khan, I. A. J. Liq. Chrom. Rel. Tech. 2003, 26.
33. (c) Nacro, K.; Bienfait, B.; Lee J.; Han, K. C.; Kang J. H.; Benzaria S.; Lewin, N. E.; Bhattacharyya, D. K.; Blumberg, P. M.; Marquez, V. E. J. Med. Chem. 2000, 43, 921.
34. (a) Stille, J. K.; Divakarumi, R. J. Am. Chem. Soc., 1975, 97, 674.
35. (b) Stille J. K.; Divakarumi, R. J. Am. Chem. Soc., 1978, 100, 1303.
36. Cowell, A.; Stille, J. K. J. Am. Chem. Soc., 1980, 102, 4193.
37. Qing, F. L.; Jiang, Z. X. J. Fluorine Chem., 2002, 114, 177.
38. Jiang Z. X.; Qing F. L Tetrahedron Lett., 2001, 42, 9051.
39. Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc., 1990, 112, 6120.
40. (a) Gabriele, B.; Salerno, G.; De Pascah, F.; Costa M.; Chiusoli G. P. J. Chem. Soc., Perkin Trans. 1, 1997, 147.
41. (b) Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Chem. Commun., 1994, 1429.
42. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed., University Science Books, Sausalito, 1987.
43. (b) Heck, R. F. Organic Synthesis via Metal Carbonyls, Vol. 1 (Eds.: I. Wender, P. Pino), Interscience Publishers, New York, 1968, pp. 373-404.
44. (e) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994.
45. Yang, H. W.; Romo, D. Tetrahedron, 1999, 55, 6403.
46. (a) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414.
47. (b) Magriotis, P. A. Angew. Chem. 2001, 113, 4507
48. Magriotis, P. A. Angew. Chem. Int. Ed. 2001, 40, 4377.
49. Müller, H. M.; Seebach, D. Angew. Chem. 1993, 105, 483
50. Müller, H. M.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1993, 32, 477.
51. (a) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta, 1996, 79, 913.
52. (b) Cheng, R. P.; Gellman, S. H.; De Grado, W. F. Chem. Rev., 2001, 101, 3219.
53. (c) Cheng, J. J.; Deming, T. J. J. Am. Chem. Soc. 2001, 123, 9457.
54. (d) Jia, L.; Ding, E.; Anderson, W. R. J. Chem. Soc., Chem. Commun., 2001, 1436.
55. (e) Allmendinger, M.; Eberhardt, R.; Luinstra, G.; Rieger, B. J. Am. Chem. Soc., 2002, 124, 5646.
56. (a) Chamchaang, W.; Pinhas, A. R. J. Chem. Soc., Chem. Commun., 1988, 710.
57. (b) Chamchaang, W.; Pinhas, A. R. J. Org. Chem., 1990, 55, 2943.
58. (c) Ley, S. V.; Middleton, B. J. Chem. Soc., Chem. Commun., 1998, 1995.
59. For Co-catalyzed aziridine carbonylations, see: (a) Piotti, M. E.; Alper, H. J. Am. Chem. Soc., 1996, 118, 111.
60. (b) Davoli, P.; Moretti, I.; Prati, F.; Alper, H. J. Org. Chem., 1999, 64, 518.
61. (c) Davoli, P.; Prati, F. Heterocycles, 2000, 53, 2379.
62. (d) Lee, J. T.; Thomas, P. J.; Alper, H. J. Org. Chem., 2001, 66, 5424.
63. (e) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron, 2001, 57, 1801. For Rh-catalyzed aziridine carbonylations, see
64. (f) Alper, H.; Urso, F.; Smith, D. J. H. J. Am. Chem. Soc., 1983, 105, 6737.
65. (g) Roberto, D.; Alper, H. Organometallics, 1984, 3, 1767.
66. (h) Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc., 1989, 111, 931. For Pd-catalyzed aziridine carbonylations, see
67. (i) Alper, H.; Hamel, N. Tetrahedron Lett., 1987, 28, 3237.
68. (j) Spears, G. W.; Nakanishi, K.; Ohfune, Y. Synlett, 1991, 91.
69. (k) Tanner, D.; Somfai, P. Bioorg. Med. Chem. Lett., 1993, 3, 2415.
70. (a) Drent, E.; Kragtwijk E. Shell Internationale Research B. V. Maatschappij, Neth., EP 577206, 1994 [Chem. Abstr., 1994, 120, 19 1517c].
71. (b) Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem. Int. Ed., 2002, 41, 2781.
72. 8 to carbonylate ethylene oxide to oligomeric polyesters, see: Hattori, N.; Nishida, H. (Tokuyama Soda Co.). Jpn. Pat. 09169753; Chem. Abstr., 1997, 127, 95188.
73. (a) Kamiya, Y.; Kawato, K.; Ohta, H. Chem. Lett., 1980, 1549.
74. (b) Bates, R. W.; Fernandez-Moro, R.; Ley, S. V. Tetrahedron, 1991, 47, 9929.
75. (c) Shimizu, I.; Maruyama, T.; Makuta, T.; Yamamoto, Y. Tetrahedron Lett., 1993, 34, 2135.
76. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E.; Coates, G. W. J. Am. Chem. Soc., 2002, 124, 1174.
77. Van den Hoven, B. G.; El Ali, B.; Alper, H. J. Org. Chem. 2000, 65, 4131.
78. El Ali, B.; Alper, H. J. Org. Chem., 1991, 56, 5357.
79. Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett., 1999, 40, 989.
80. Fukuta, Y.; Matsuda, I.; Itoh K. Tetrahedron Lett. 2001, 42, 1301.
81. Yoneda, E.; Kaneko, T.; Zhang, S. W.; Onitsuka, K.; Takahashi, S. Org. Lett., 2000, 2, 441,
82. Qing F. L.; Jiang Z. X. Tetrahedron Lett., 2001, 42, 5933.
83. (a) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun., 1985, 511.
84. (b) Alper, H.; Leonard, D. Tetrahedron Lett., 1985, 26, 5639.
85. Tezuka, K. Y.; Ishizaki, Y.; Inoue, Y. J. Mol. Catal., 1998, 129, 199.
86. (a) Norton, J. R.; Shenton, K. E.; Schwartz, J. Tetrahedron Lett., 1975, 16, 51.
87. (b) Murray, T. F.; Samsel, E. G.; Varma, V.; Norton, J. R. J. Am. Chem. Soc., 1981, 103, 7520.
88. Ogawa, A.; Kawabe, K.; Kawakami, J.; Mihara, M.; Hirao, T.; Sonoda, N. Organometallics, 1998, 17, 3111.
89. Aristoff, P. A.; Johnson, P. D.; Harrison, A. W. J. Am. Chem. Soc., 1985, 107, 7967.
90. Wu, G.Z.; Shimoyama, I.; Negishi, E. J. Org. Chem., 1991, 56, 6506.
91. Ciattini, P. G.; Mastropietro, G.; Morera, E.; Ortar, G. Tetrahedron Lett., 1993, 34, 3763.
92. Negishi, E.; Copéret, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. J. Am. Chem. Soc., 1996, 118, 5904.
93. Grigg, R.; Khlil, H.; Levett, P.; Virica, J.; Sridharan, V. Tetrahedron Lett., 1994, 35, 3197.
94. El Ali, B.; Okuro, K.; Vasapollo, G.; Alper, H. J. Am. Chem. Soc., 1996, 118, 4264.
95. Vasapollo, G.; Mele, G.; Maffei, A.; Del Sole R. Appl. Organomet. Chem., 2003, 17, 835.
96. Vasapollo, G.; Scarpa, A.; Mele, G.; Ronzini, L.; El Ali, B. Appl. Organomet. Chem., 2000, 14, 739.
97. Vasapollo, G.; Mele, G.; El Ali, B. J. Mol. Cat. A. 2003, 204-205, 97.
98. (a) Tanner, D. Angew. Chem. Int. Ed. 1994, 33, 599.
99. (b) Bucciarelli, M.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Chem. Soc., Perkin Trans. 1, 1993, 3041.
100. Bonardi, A.; Costa, M.; Gabriele, B.; Salerno, G.; Chiusoli, G.P. Tetrahedron Lett. 1995, 36, 7495.
101. Copéret, C.; Sugihara, T.; Negishi, E. Tetrahedron Lett. 1995, 40, 1771.
102. Copéret, C.; Shengming, M.; Sugihara, T.; Negishi, E. Tetrahedron, 2000, 56, 11529.
103. Berger, D.; Imhof, W. Tetrahedron, 2000, 56, 2015.
104. Matsuda, A. Bull. Chem. Soc. Jap., 1968, 41, 1876.
105. Falbe, J.; Korte, F. Chem. Ber., 1965, 28, 1928.
106. Knifton, J. F. J. Organomet. Chem., 1980, 188, 223.
107. Jergorov, A.; Trnka, T.; Turecek, F.; Hanus, V. J. Mol. Cat., 1990, 63, 335.
108. Zhou, J. Q.; Alper, H. J. Org. Chem. 1992, 57, 3328.
109. Bertozzi, S.; Salvatori, P. Synth. Commun., 1996, 26, 2959.
110. Dong Doan, H.; Gore, J.; Vatèle, J. M. Tetrahedron Lett., 1999, 40, 6765.
111. Longo, L.; Mele, G.; Ciccarella, G.; Sgobba, V.; El Ali, B.; Vasapollo, G. Appl. Organomet. Chem., 2002, 16, 537.
112. Kang, S. K.; Kim, K. J.; Yu, C. M.; Hwang, J. W.; Do, Y. K. Org. Lett., 2001, 3, 2851.
113. Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem., 2000, 65, 9230.
114. Hirao, K.; Morii, N.; Joh, T.; Takahashi, S. Tetrahedron Lett., 1995, 36, 6243.
115. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem., 2001, 4607.
116. (a) Schore, N. E. In Comprehensive Organometallic Chemistry II, Hegedus, L. S., Ed.; Pergamon: Kidlington, 1995; Vol. 12, pp. 703 and references within.
117. (b) Jeong, N.; Hwang, S. H,; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc., 1994, 116, 3159.
118. (c) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc., 1994, 116, 8793.
119. (d) Pagenkopf, B. L.; Livinghouse, T. J. J. Am. Chem. Soc., 1996, 118, 2285.
120. (a) Kool, L. B.; Rausch, M. D.; Alt, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl., 1985, 24, 394.
121. (b) Binger, P.; Müller, P.; Benn, R.; Rufinska, A.; Gabor, B.; Krüger, C.; Betz, P. Chem. Ber. 1989, 122, 1035.
122. (c) Hewlett, D. F.; Whitby, R. J. J. Chem. Soc., Chem. Commun., 1990, 1684.
123. (d) Mashima, K.; Haraguchi, H.; Oyoshi, A.; Sakai, N.; Takaya, H. Organometallics, 1991, 10, 2731.
124. (e) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc., 1995, 117, 6787.
125. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc., 1995, 117, 6785.
126. Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc., 1996, 118, 1557.
127. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc., 1997, 119, 4424.
128. Mandal, S. K.; Amin, S. R.; Crowe, W. E. J. Am. Chem. Soc., 2001, 123, 6457.
129. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc., 1996, 118, 5818.
130. Ojima, I.; Donovan, R. J.; Shay, W. R. J. Am. Chem. Soc., 1992, 114, 6580.
131. Shibata, T.; Takagi, K. J. Am. Chem. Soc., 2000, 122, 9852.
132. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Tetrahedron Lett., 2004, 45, 9163.
133. Mastrorilli, P.; Nobile, C. F.; Paolillo R.; Suranna G. P. J. Mol. Cat. (A), 2004, 214, 103.
134. Troisi, L.; Vasapollo, G.; El Ali, B.; Mele, G.; Florio, S.; Capriati, V. Tetrahedron Lett., 1999, 40, 1771.
135. Lenoble, G.; Naigre, R.; Chenal, T.; Urrutigoity, M.; Daran, J. C.; Klack, P. Tetrahedron Asymm., 1999, 10, 929.
136. Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Asymm., 1999, 10, 1163.
137. Catellani, M.; Chiusoli, G.P.; Fagnola, M.F.; Solari, G. Tetrahedron Lett., 1994, 35. 5923.
138. Catellani, M.; Chiusoli, G. P.; Marzolini, G.; Rossi, E. J. Organomet. Chem., 1996, 65, 525.
139. Yoneda, E.; Sugioka, T.; Hirao, K.; Zhang, S. W.; Takahashi, S. J. Chem. Soc., Perkin. Trans. 1, 1998, 477.
140. Kadnikov D. V.; Larock, R.C. Org. Lett., 2000, 2, 3643.
141. Park, K. H.; Jung, I. G.; Chung, Y. K. Synlett, 2004, 14, 2541.
142. Amorati, R.; Attanasi, O. A.; El Ali, B.; Filippone, P.; Mele, G.; Spadavecchia, J.; Vasapollo, G. Synthesis, 2002, 2749.
143. Boeckman, R. K., Jr.; Reed, J. E.; Ge, P. Org. Lett., 2001, 3, 3651.
144. (a) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. J. Chem. Soc., Chem. Commun., 1997, 1209.
145. (b) Chiusoli, G. P.; Costa, M,; Gabriele, B.; Salerno, G. J. Mol. Catal. A 1999, 143, 297.
146. Lenoble, G.; Urrutigoity, M.; Kalck, P. Tetrahedron Lett. 2001, 42, 3697.
147. Yoneda, E.; Zhang, S. W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459.
148. Orejon, A.; Alper, H. J. Mol. Catal. A 1999, 143, 137.
149. Maffei, A.; Mele, G.; Ciccarella, G.; Vasapollo, G.; Crisafulli, C.; Scirè, S.; La Mantia, F. Appl. Organomet. Chem., 2002, 16, 543.
150. Chanthateyanonth, R.; Alper, H. Adv. Synth. Catal., 2004, 346, 1375.
151. (a) Doyle, M. P. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I.; Ed.; Wiley-VCH, Publishers: New York, 2000; 191.
152. b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York 1994.
153. c) Lin, G. Q.; Li, Y.M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis; Wiley: New York, 2001.
154. Alper, H.; Hamel, N. J. Chem. Soc., Chem. Comm., 1990, 135.
155. Cao, P.; Zhang, X. J. Am. Chem, Soc., 1999, 121, 7708.
156. Brunner, M.; Alper, H. J. Org. Chem., 1997, 62, 7565.
157. Hayashi, T.; Tang, J.; Kato, K. Org. Lett., 1999, 1, 1487.
158. Okuro, K.; Kai, H.; Alper, H. Tetrahedron Asymm., 1997, 8, 2307.
159. Tetrahedron Asymm., 2004, 15, 35.
160. Dong, C.; Alper, H., J. Org. Chem., 2004, 69, 5011.
161. Vasapollo, G.; Mele, G. Can. J. Chem., 2005, 83, 674.
162. (a) Clòaessens, C. G.; Blau, W. J.; Cook, M.; Hanack, M.; Nolte, R. J. M.; Torres, T.; Wöhrle, D. Monatsh. Chem. 2001, 132, 3 and references therein.
163. (b) Leznof, C.C.; Lever, A. B. P. Phthalocyanines: Properties and Applications, Vols 1-4. VCH: Weinheim, 1989-1996.
164. (a) McKeown, N. B. Phthalocyanines Materials Synthesis Structure and Function; Cambridge University Press: Cambridge, 1998.
165. (b) Gürek, A. G.; Bekaroglu, O. J. of Porphyrins Phthalocyanines, 1997, 1, 67.
166. (c) Gürek, A.G.; Bekaroglu, O. J. of Porphyrins Phthalocyanines, 1997, 1, 227.
167. (d) Polley R, Heckmann H, Hanack M. In Houben-Weyl; 4th ed. Vol E9; Thieme, Stuttgart, 1997; 718.
168. Hirsch, A. The Chemistry of the Fullerenes; Georg Thieme Verlag: Stuttgart, 1994.
169. Hebard, A. F.; Rosseinsky, M. J.; Haddon, R. C.; Murphy, D. W.; Glarum, S. H.; Palstra, T. T. M.; Ramirez, A. P.; Kortan, A. R. Nature, 1991, 350, 600.
170. Wang, P.; Metzger R. M.; Bandow, S.; Maruyama, Y. J. Phys. Chem. 1993, 97, 2926.
171. Wang, P.; Maruyama, Y.; Metzger, R. M. Langmuir, 1996, 12, 3932.
172. Thomas, K. G.; Biju, V.; Guldi, D. M.; Kamat, P. V.; George, M. V. J. Phys. Chem. A, 1999, 103, 10755.
173. Da-Ros, T.; Prato, M.; Guldi, D. M; Alessio, E.; Ruzzi, M.; Pasimeni, L. J. Chem. Soc., Chem. Commun., 1999, 635.
174. D'Souza, F.; Deviprasad, G. R.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc., 2001, 123, 5277.
175. Wang, P.; Metzger, R. M.; Chen B. Thin Solids Flims, 1998, 327-329, 96.
176. Shi, X.; Caldwell, W.B.; Chen, K.; Mirkin C.A. J. Am. Chem. Soc., 1994, 116, 11598.
177. Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc., 1993, 115, 9798.