[N]Phenylenes: A Novel Class of Cyclohexatrienoid Hydrocarbon

Carbon-Rich Compounds: From Molecules to Materials

Volumn , Issue , 2006, Pages 140-197

  Miljanić, Ognjen Š ^a,b   Vollhardt, K Peter C ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

N phenylenes; Comparative reactivity of the phenylenes; Cyclohexatrienoid hydrocarbon; Physical properties of the phenylenes; Preparation of phenylenes

Indexed keywords

EID: 84891027561     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527607994.ch4     Document Type: Chapter

References (213)

1. V. I. Minkin, M. N. Glukhovtsev, B. Ya. Simkin, Aromaticity and Antiaromaticity: Electronic and Structural Aspects, Wiley, New York, 1994;
2. P. J. Garratt, Aromaticity, Wiley, New York, 1986;
3. Chem. Rev. 2001, 101, 1115-1566, Special Issue: Aromaticity (some of the reviews from this issue are also cited separately).
4. T. M. Krygowski, M. K. Cyrański, Chem. Rev. 2001, 101, 1385-1419 and references cited therein.
5. L. J. Schaad, B. A. Hess, Jr., Chem. Rev. 2001, 101, 1465-1476 and references cited therein;
6. S. W. Slayden, J. F. Liebman, Chem. Rev. 2001, 101, 1541-1566 and references cited therein.
7. R. H. Mitchell, Chem. Rev. 2001, 101, 1301-1315 and references cited therein;
8. J. A. N. F. Gomes, R. B. Mallion, Chem. Rev. 2001, 101, 1349-1383 and references cited therein.
9. J. W. Armit, R. Robinson, J. Chem. Soc., (Abstracts) 1925, 127, 1604-1618;
10. J. Kruszewski, T. M. Krygowski, Tetrahedron Lett. 1970, 11, 319-324;
11. T. M. Krygowski, Tetrahedron Lett. 1970, 11, 1311-1312;
12. W. T. Dixon, J. Chem. Soc. B 1970, 612-616.
13. M. K. Cyrañski, T. M. Krygowski, A. R. Katrizky, P. v. R. Schleyer, J. Org. Chem. 2002, 67, 1333-1338.
14. K. Jug, A. M. Köster, J. Phys. Org. Chem. 1991, 4, 163-169;
15. A. R. Katrizky, P. Barczynski, G. Masumarra, D. Pisano, M. Szafan, J. Am. Chem. Soc. 1989, 111, 7-15.
16. G. A. Jeffrey, J. R. Ruble, R. K. Mcmulian, J. A. Pople, Proc. R. Soc. London, Ser. A 1987, 414, 47-57.
17. H. Irngartinger, M. Nixford, Angew. Chem. 1983, 95, 415-416; Angew. Chem., Int. Ed. Engl. 1983, 22, 403-404;
18. A. Sekiguchi, M. Tanaka, T. Matsuo, H. Watanabe, Angew. Chem. 2001, 113, 1721-1723; Angew. Chem. Int. Ed. 2001, 40, 16751677.
19. A. A. Deniz, K. S. Peters, G. J. Snyder, Science 1999, 286, 1119-1122.
20. M. Faraday, Philos. Trans. R. Soc. London 1825, 115, 440-466.
21. O. L. Chapman, C. L. Mcintosh, J. Pacansky, J. Am. Chem. Soc. 1973, 95, 614-617;
22. A. Krantz, C. Y. Lin, M. D. Newton, J. Am. Chem. Soc. 1973, 95, 2744-2746.
23. R. D. Kennedy, D. Lloyd, H. Mcnab, J. Chem. Soc., Perkin Trans 1 2002, 1601-1621 and references cited therein.
24. E. Hückel, Grundzüge der Theorie ungesättigter und aromatischer Verbindungen, Verlag Berlin, 1938;
25. E. Hückel, Z. Phys. 1931, 70, 204286.
26. W. C. Lothrop, J. Am. Chem. Soc. 1941, 63, 1187-1191.
27. M. K. Shepherd, Cyclobutarenes: The Chemistry of Benzocyclobutene, Biphenylene, and Related Compounds, Elsevier, New York, 1991;
28. F. Toda, P. J. Garratt, Chem. Rev. 1992, 92, 1685-1707.
29. Sigma-Aldrich Fine Chemicals Catalog, 2003-2004.
30. M. Iyoda, S. M. H. Kabir, A. Vorasingha, Y. Kuwatani, M. Yoshida, Tetrahedron Lett. 1998, 39, 5393-5396.
31. S. Kanoktanapora, J. A. H. Macbride, J. Chem. Res. (S) 1980, 203-207;
32. J. A. Macbride, J. Chem. Soc., Chem. Commun. 1972, 12191220.
33. J. P. Droske, J. K. Stille, Macromolecules 1984, 17, 1-10;
34. L. Friedman, D. F. Lindow, J. Am. Chem. Soc. 1968, 90, 2324-2328;
35. D. F. Lindow, L. Friedman, J. Am. Chem. Soc. 1967, 89, 1271-1272.
36. C. Perthuisot, B. L. Edelbach, D. L. Zubris, N. Simhai, C. N. Iverson, C. Mülier, T. Satoh, W. D. Jones, J. Mol. Catal. A 2002, 189, 157-168 and references cited therein.
37. H. Jeany, K. G. Mason, J. M. Sketchiey, Tetrahedron Lett. 1970, 11, 485-488.
38. H. Heaney, P. Lees, Tetrahedron Lett. 1964, 5, 3049-3052.
39. A. Yokozeki, C. F. Wilcox, S. H. Bauer, J. Am. Chem. Soc. 1974, 96, 1026-1032;
40. J. K. Fawcett, J. Trotter, Acta Crystallogr. 1966, 20, 87-93;
41. T. C. W. Mak, J. Trotter, J. Chem. Soc. 1962, 1-8.
42. H. Yamaguchi, M. Ata, J. F. W. Mcomie, J. W. Barton, H. Baumann, J. Chem. Soc., Faraday Trans. 2 1983, 79, 599-609.
43. H. P. Figeys, N. Defay, R. H. Martin, J. F. W. Mcomie, B. E. Ayers, J. B. Chadwick, Tetrahedron 1976, 32, 2571-2578.
44. A. J. Jones, P. J. Garratt, K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl. 1973, 12, 241-243; Angew. Chem. 1973, 85, 260-261.
45. Z. B. Maksić, M. Eckert-Maksić, O. Mó, M. Yáñez, in Pauling's Legacy: Modern Modelling of the Chemical Bond, Z. B. Maksić, W. J. Orviiie-Thomas (eds.). Elsevier: Amsterdam, 1999, 47-101 and references cited therein;
46. A. Stanger, N. Ben-Mergui, S. Perl, Eur.J. Org. Chem. 2003, 2709-2712;
47. A. Stanger, E. Tkachenko, J. Comput. Chem. 2001, 22, 1377-1386;
48. A. Stanger, J. Am. Chem. Soc. 1998, 120, 12034-12040;
49. N. L. Frank, J. S. Siegel, in Advances in Theoretically Interesting Molecules, R. P. Thummel (ed.), JAI: London, 1995, Vol. 3, pp. 209-261;
50. J. S. Siegel, Angew. Chem., Int. Ed. Engl. 1994, 33, 1721-1723; Angew. Chem. 1994, 106, 1808-1810 references cited therein;
51. K. Jug, P. C. Hiberty, S. Shaik, Chem. Rev. 2001, 101, 1477-1500 and references cited therein.
52. S. Shaik, A. Shurki, D. Dano-vich, P. C. Hiberty, Chem. Rev. 2001, 101, 1501-1539 and references cited therein;
53. P. C. Hiberty, D. Danovich, A. Shurki, S. Shaik, J. Am. Chem. Soc. 1995, 117, 7760-7768 and references cited therein. For a popular account:
54. G. Narahari Sastry, Curr. Sci. 2001, 81, 1288-1290.
55. C. S. Wannere, K. W. Sattelmeyer, H. F. Schaefer III, P. v. R. Schleyer, Angew. Chem. 2004, 116, 4296-4302; Angew. Chem. Int. Ed. 2004, 43, 42004206.
56. M. Randić, Chem. Rev. 2003, 103, 3449-3605 and numerous references cited therein.
57. I. Gutman, S. J. Cyvin, J. Brunvoll, Monatsh. Chem. 1994, 125, 887-894. For illustration, there are 12 [5]phenylenes, 122 [7]phenylenes, and 6387 [10]phenylenes.
58. N. Trinajstić, T. G. Schmaiz, T. P. Živković, S. Nikolić, G. E. Hite, D. J. Kiein, W. A. Seitz, New J. Chem. 1991, 15, 27-31.
59. H.-D. Beckhaus, R. Faust, A. J. Matzger, D. L. Mohier, D. W. Rogers, C. Rüchardt, A. K. Sawhey, S. P. Verevkin, K. P. C. Vollhardt, S. Wolff, J. Am. Chem. Soc. 2000, 122, 7819-7820.
60. M. D. Watson, A. Fechtenkotter, K. Müllen, Chem. Rev. 2001, 101, 1267-1300 and references cited therein;
61. R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1995;
62. E. Ciar, The Aromatic Sextet, Wiley, London, 1972.
63. Recent examples: M. G. Debije, J. Piris, M. P. de Haas, J. M. Warman, Ž. Tomović, C. D. Simpson, M. D. Watson, K. Müllen, J. Am. Chem. Soc. 2004, 126, 4641-4645;
64. J. S. Wu, L. Gherghel, M. D. Watson, J. Li, Z. Wang, C. D. Simpson, U. Kolb, K. Müllen, Macromolecules 2003, 36, 7082-7089;
65. H. Meng, M. Bendikov, G. Mitchell, R. Helgeson, F. Wudl, Z. Bao, T. Siegrist, C. Kloc, C.-H. Chem, Adv. Mater. 2003, 15, 1090-1093;
66. Y. Zhang, J. R. Petta, S. Ambily, Y. Shen, D. C. Ralph, G. C. Malliaras, Adv. Mater. 2003, 15, 1632-1635;
67. C. D. Dimitrakopoulos, I. Kymissis, S. Purushothaman, D. A. Neumayer, P. R. Duncombe, R. B. Laibowitz, Adv. Mater. 1999, 11, 1372-1375.
68. I. Gutman, J. Chem. Soc., Faraday Trans. 1993, 89, 2413-2416.
69. M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153-1183 and references cited therein.
70. Ž. Tomović, I. Gutman, Hemijski Pregled, 2001, 42, 29-37 and references cited therein.
71. C. F. Wilcox, Tetrahedron Lett. 1968, 9, 795-800;
72. C. F. Wilcox, J. Am. Chem. Soc. 1969, 91, 2732-2736.
73. I. Gutman, N. Trinajstić, C. F. Wilcox, Tetrahedron 1975, 31, 143146;
74. C. F. Wilcox, I. Gutman, N. Trinajstić, Tetrahedron 1975, 31, 147152.
75. S. Nikolić, N. Trinajstić, Z. Mihalić, Croat. Chem. Acta. 1995, 68, 105-129;
76. I. Gutman, Y. N. Yeh, S. L. Lee, Y. L. Luo, Indian J. Chem. 1993, 32A, 651-661;
77. H. Wiener, J. Am. Chem. Soc. 1947, 69, 17-20.
78. Lj. Pavlović, I. Gutman, J. Chem. Inf. Comput. Sci. 1997, 37, 355-358.
79. I. Gutman, V. Ivanov-Petrovic, J. Mol. Struct. (THEOCHEM) 1997, 389, 227-232.
80. For the two earlier summaries, see: K. P. C. Vollhardt, D. L. Mohler, in Advances in Strain in Organic Chemistry, Vol. 5, B. Halton (ed.), JAI, London, 1996, 121-160;
81. K. P. C. Vollhardt, Pure. Appl. Chem. 1993, 65, 153-156.
82. E. N. Losey, E. Legoff, J. Org. Chem. 1973, 38, 3812.
83. J. W. Barton, R. B. Walker, Tetrahedron Lett. 1978, 19, 1005-1008;
84. N. C. Jamieson, G. E. Lewis, Aust. J. Chem. 1967, 20, 321-338.
85. J. W. Barton, M. K. Shepard, Tetrahedron Lett. 1984, 25, 49674970.
86. S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901-2915;
87. C. Aubert, O. Buisine, M. Petit, F. Slowinski, M. Maiacria, Pure. Appl. Chem. 1999, 71, 1463-1470;
88. D. B. Grotjahn, in Comprehensive Organometallic Chemistry II, Vol. 12, E. W. Abel, F. G. A. Stone, G. Wilkinson (eds.), L. S. Hegedus (vol. ed.), Pergamon, Oxford, 1995, pp. 741-770;
89. K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl. 1984, 23, 539-556; Angew. Chem. 1984, 96, 525-541;
90. N. Schore, Chem. Rev. 1988, 88, 1081-1119.
91. B. C. Berris, Y.-H. Lai, K. P. C. Vollhardt, J. Chem. Soc., Chem. Commun. 1982, 953-854.
92. B. C. Berris, G. H. Hovakeemian, Y.-H. Lai, H. Mestdagh, K. P. C. Vollhardt, J. Am. Chem. Soc. 1985, 107, 5670-5687.
93. M. Hirthammer, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 2481-2482.
94. J. M. Schulman, R. L. Disch, J. Am. Chem. Soc. 1996, 118, 8470-8474 and references cited therein.
95. B. C. Berris, G. H. Hovakeemian, K. P. C. Vollhardt, J. Chem. Soc., Chem. Commun. 1983, 502-503.
96. L. Bianco, H. E. Helson, M. Hirthammer, H. Mestdagh, S. Spyroudis, K. P. C. Vollhardt, Angew. Chem. 1987, 99, 1276-1277; Angew. Chem., Int. Ed. Engl. 1987, 26, 1246-1247.
97. D. Holmes, S. Kumaraswamy, A. J. Matzger, K. P. C. Vollhardt, Chem. Eur. J. 1999, 5, 3399-3412 and unpublished results.
98. R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 268-270; Angew. Chem., Int. Ed. Engl. 1986, 25, 266-268.
99. R. H. Schmidt-Radde, K. P. C. Vollhardt, J. Am. Chem. Soc. 1992, 114, 9713-9715.
100. R. Diercks, B. E. Eaton, S. Gurtzgen, S. Jalisatgi, A. J. Matzger, R. H. Radde, K. P. C. Vollhardt, J. Am. Chem. Soc. 1998, 120, 8247-8248.
101. P. I. Dosa, G. D. Whitener, K. P. C. Vollhardt, A. D. Bond, S. J. Teat, Org. Lett. 2002, 4, 2075-2078.
102. K. Jonas, E. Deffense, D. Habermann, Angew. Chem. 1983, 95, 729; Angew. Chem., Int. Ed. Engl. 1983, 22, 716-717.
103. R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271; Angew. Chem., Int. Ed. Engl. 1986, 25, 268269.
104. R. Diercks, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 3150-3152.
105. S. Han A. D. Bond, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3357-3361; Angew. Chem. Int. Ed. 2002, 41, 32233227.
106. J. M. Schulman, R. L. Disch, J. Phys. Chem. A 1997, 101, 5596-5599.
107. H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, pp. 321-330;
108. F. Vögtle, Fascinating Molecules in Organic Chemistry, Wiley, New York, 1992, pp. 156-180;
109. K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76;
110. W. H. Laarhoven, W. J. C. Prinsen, Top. Curr. Chem. 1984, 125, 63-130.
111. C. Eickmeier, H. Junga, A. J. Matzger, F. Scherhag, M. Shim, K. P. C. Vollhardt, Angew. Chem. 1997, 109, 2194-2199; Angew. Chem., Int. Ed. Engl. 1997, 36, 2103-2108.
112. S. Han, D. R. Anderson, A. D. Bond, H. V. Chu, R. L. Disch, D. Hoimes, J. M. Schuiman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3361-3364; Angew. Chem. Int. Ed. 2002, 41, 3227-3230.
113. J. M. Schulman, R. L. Disch, J. Phys. Chem. A 2003, 107, 5223-5227.
114. J. M. Schulman, R. L. Disch, Chem. Phys. Lett. 1996, 262, 813-816;
115. A. D. J. Haymet, Chem. Phys. Lett. 1985, 122, 421-424.
116. B. T. Dunlap, R. Taylor, J. Phys. Chem. 1994, 98, 11018-11019.
117. C. Eickmeier, D. Holmes, H. Junga, A. J. Matzger, F. Scherhag, M. Shim, K. P. C. Vollhardt, Angew. Chem. 1999, 111, 856-860; Angew. Chem., Int. Ed. Engl. 1999, 38, 800804.
118. D. T.-Y. Bong, L. Gentric, D. Holmes, A. J. Matzger, F. Scherhag, K. P. C. Vollhardt, Chem. Commun. 2002, 278-279.
119. D. T.-Y. Bong, E. W. L. Chan, R. Diercks, P. I. Dosa, M. M. Haley, A. J. Matzger, O. Š. Miijanić, K. P. C. Voiihardt, A. D. Bond, S. J. Teat, A. Stanger, Org. Lett. 2004, 6, 22492252.
120. H. Hart, K. Katsumasa, C.-J. F. Du, J. Org. Chem. 1985, 50, 3104-3110.
121. M. B. Goldfinger, K. B. Crawford, T. M. Swager, J. Am. Chem. Soc. 1997, 119, 4578-4593.
122. R. Boese, A. J. Matzger, D. L. Mohler, K. P. C. Vollhardt, Angew. Chem. 1995, 107, 1630-1633; Angew. Chem., Int. Ed. Engl. 1995, 34, 14781481.
123. J. E. Anthony, S. I. Khan, Y. Rubin, Tetrahedron Lett. 1997, 38, 3499-3502.
124. P. N. Baxter, J. Org. Chem. 2001, 66, 4170-4179.
125. D. Bruns, H. Miura, K. P. C. Vollhardt, A. Stanger, Org. Lett. 2003, 5, 549-552.
126. P. v. R. Schleyer, H. Jiao, Angew. Chem. 1996, 108, 2548-2551; Angew. Chem., Int. Ed. Engl. 1996, 35, 23832386;
127. J. Aihara, J. Chem. Soc., Faraday Trans. 1995, 91, 237-239;
128. D. Babic, N. Trinajstic, J. Mol. Struct. (THEOCHEM) 1994, 314, 321327;
129. I. Gutman, S. J. Cyvin, J. Mol. Struct. (THEOCHEM) 1993, 288, 85-91;
130. J. Aihara, Bull. Chem. Soc. Jpn. 1993, 66, 57-60;
131. J. Aihara, J. Am. Chem. Soc. 1992, 114, 865-868;
132. J. Cioslowski, P. B. O'Connor, E. D. Fleischmann, J. Am. Chem. Soc. 1991, 113, 1086-1089.
133. A. J. Matzger, M. Shim, K. P. C. Vollhardt, Chem. Commun. 1999, 1871-1872;
134. O. Š. Miljanić, K. P. C. Vollhardt, G. D. Whitener, Synlett 2003, 29-34.
135. H. A. Staab, F. Diederich, Chem. Ber. 1983, 116, 3487-3503;
136. H. A. Staab, F. Diederich, C. Krieger, D. Schweitzer, Chem. Ber. 1983, 116, 3504-3512.
137. I. D. Campbell, G. Eglinton, W. Henderson, R. A. Raphael, Chem. Commun. 1966, 87-89;
138. D. Solooki, J. D. Ferrara, D. Malaba, J. D. Bradshaw, C. A. Tessier, W. J. Youngs, Inorg. Synth. 1997, 31, 122128;
139. C. Huynh, G. Linstrumelle, Tetrahedron 1988, 44, 6337-6344;
140. M. Iyoda, A. Vorasingha, Y. Kuwatani, M. Yoshida, Tetrahedron Lett. 1998, 39, 4701-4704.
141. H. A. Staab, F. Graf, Tetrahedron Lett. 1966, 7, 751-757;
142. H. A. Staab, F. Graf, Chem. Ber. 1970, 103, 1107-1118.
143. U. H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev. 1999, 28, 107-119;
144. F. Diederich, Nature 1994, 369, 199-207.
145. V. R. Coluci, D. S. Galvão, R. H. Baughman, J. Chem. Phys. 2004, 121, 3228-3237;
146. N. Narita, S. Nagai, S. Suzuki, Phys. Rev. B 2001, 64, 245408/1-245408/7;
147. N. Narita, S. Nagai, S. Suzuki, K. Nakao, Phys. Rev. B 2000, 62, 11146-11151;
148. N. Narita, S. Nagai, S. Suzuki, K. Nakao, Phys. Rev. B 1998, 58, 1100911014;
149. M. M. Haley, Synlett 1998, 557-565.
150. G. H. Hovakeemian, K. P. C. Vollhardt, Angew. Chem. 1983, 96, 1001-1002; Angew. Chem., Int. Ed. Engl. 1983, 22, 994-996.
151. D. L. Mohler, K. P. C. Vollhardt, S. Wolff, Angew. Chem. 1990, 102, 1200-1202; Angew. Chem., Int. Ed. Engl. 1990, 29, 1151-1154.
152. R. L. Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker, New York/Basel/Hong Kong, 1996.
153. A. Soncini, R. W. A. Havenith, P. W. Fowler, L. W. Jenneskens, E. Steiner, J. Org. Chem. 2002, 67, 4753-4758;
154. P. F. Fowler, R. W. A. Havenith, L. W. Jenneskens, A. Soncini, E. Steiner, Chem. Commun. 2001, 2386-2387.
155. O. Š. Miljanić, K. P. C. Vollhardt, unpublished results.
156. R. Jeyaraman, R. W. Murray, J. Am. Chem. Soc. 1984, 106, 2462-2463;
157. R. Murray, R. Jeyaraman, J. Org. Chem. 1985, 50, 2847-2853;
158. W. Adam, Y.-Y. Chan, D. Cremer, J. Gauss, D. Scheutzow, M. Schindler, J. Org. Chem. 1987, 52, 2800-2803;
159. W. Adam, R. Curci, J. O. Edwards, Acc. Chem. Res. 1989, 22, 205-211.
160. W. Adam, M. Balci, H. Kiliç, J. Org. Chem. 1998, 63, 8544-8546.
161. S. Kumaraswamy, S. S. Jalisatgi, A. J. Matzger, O. Š. Miljanić, K. P. C. Vollhardt, Angew. Chem. 2004, 116, 3797-3801; Angew. Chem. Int. Ed. 2004, 43, 3711-3715.
162. A. S. Kende, P. T. Macgregor, J. Am. Chem. Soc. 1964, 86, 2088-2089.
163. J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron 1968, 24, 5358.
164. F. Sevin, M. L. Mckee, J. Am. Chem. Soc. 2001, 123, 4591-4600 and references cited therein.
165. H. Mestdagh, K. P. C. Vollhardt, J. Chem. Soc., Chem. Commun. 1986, 281-282.
166. J. J. Gajewski, Hydrocarbon Thermal Isomerizations, Academic Press, New York, 1981;
167. R. G. Harvey, Curr. Org. Chem. 2004, 8, 303-323;
168. L. T. Scott, Angew. Chem. 2004, 116, 5102-5116; Angew. Chem. Int. Ed. 2004, 43, 4994-5007.
169. U. Wiersum, L. W. Jenneskens, Tetrahedron Lett. 1993, 34, 6615-6618.
170. For recent mechanistic reviews, see: A. Necula, L. T. Scott, J. Anal. Appl. Pyrol. 2000, 54, 65-87;
171. R. F. C. Brown, Eur. J. Org. Chem. 1999, 3211-3222.
172. P. I. Dosa, A. S. Schleifenbaum, K. P. C. Vollhardt, Org. Lett. 2001, 3, 1017-1020.
173. A. J. Matzger, K. P. C. Vollhardt, Chem. Commun. 1997, 1415-1416.
174. D. V. Preda, L. T. Scott, Org. Lett. 2000, 2, 1489-1492.
175. M. Oh, K. Yu, H. Li, E. J. Watson, G. B. Carpenter, D. A. Sweigart, Adv. Synth. Catal. 2003, 345, 1053-1060 and references cited therein;
176. C. Perthuisot, B. L. Edelbach, D. L. Zubris, W. D. Jones, Organometallics 1997, 16, 2016-2023.
177. Y. Oprunenko, I. Gloriozov, K. Lyssenko, S. Malyugina, D. Mityk, V. Mstisiavsky, H. Günther, G. von Firks, M. Ebener, J. Organomet. Chem. 2002, 656, 27-42;
178. C. A. Duliaghan, G. B. Carpenter, D. A. Sweigart, Chem. Eur. J. 1997, 3, 75-78;
179. C. Elschenbroich, J. Schneider, W. Massa, G. Baum, H. Mellinghoff, J. Organomet. Chem. 1988, 355, 163-176.
180. A. Ceccon, A. Gambaro, A. M. Romanin, A. Venzo, J. Organomet. Chem. 1982, 239, 345-351.
181. M. Nambu, J. S. Siegel, J. Am. Chem. Soc. 1988, 110, 3675-3676.
182. M. Nambu, K. Hardcastle, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 369-371.
183. M. Nambu, D. L. Mohler, K. Hardcastle, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1993, 115, 6138-6142.
184. R. D. Brown, P. D. Godfrey, B. T. Hart, A. L. Ottrey, M. Onda, M. Woodruff, Aust. J. Chem. 1983, 36, 639-648.
185. A. Schleifenbaum, N. Feeder, K. P. C. Vollhardt, Tetrahedron Lett. 2001, 42, 7329-7332.
186. W. V. Volland, E. R. Davidson, W. T. Borden, J. Am. Chem. Soc. 1979, 101, 533-537;
187. N. L. Allinger, J. Am. Chem. Soc. 1958, 80, 1953-1955;
188. N. L. Allinger, J. T. Sprague, J. Am. Chem. Soc. 1972, 94, 5734-5747;
189. D. W. Rogers, H. V. Voitkenberg, N. L. Allinger, J. Org. Chem. 1978, 43, 360-361;
190. W. L. Mock, Tetrahedron Lett. 1972, 475478;
191. L. Radom, J. A. Pople, W. L. Mock, Tetrahedron Lett. 1972, 479482.
192. E. J. Petersson, J. C. Fanuele, M. R. Nimlos, D. M. Lemal, G. B. Ellison, J. G. Radziszewski, J. Am. Chem. Soc. 1997, 119, 11122-11123;
193. M. Bremer, P. v. R. Schleyer, U. Fleischer, J. Am. Chem. Soc. 1989, 111, 1147-1148.
194. C. De Rango, G. Tsoucaris, J. P. Declerq, G. Germain, J. P. Putzeys, Acta Crystallogr. Sect. C 1973, 2, 189192.
195. T. E. M. Van Den Hark, P. T. Beurskens, Acta Crystallogr. Sect. C 1976, 5, 247-252;
196. P. T. Beurskens, G. Beurskens, T. E. M. Van Den Hark, Acta Crystallogr. Sect. C 1976, 5, 241-246.
197. P. V. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. Van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
198. P. V. R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. Van Eikema Hommes, Org. Lett. 2001, 3, 24652468.
199. J. M. Schulman, R. L. Disch, H. Jiao, P. v. R. Schleyer, J. Phys. Chem. A 1998, 102, 8051-8055.
200. W. Adcock, B. D. Gupta, T. C. Khor, D. Doddrell, W. Kitching, J. Org. Chem. 1976, 41, 751-759.
201. R. P. Thummel, W. Nutakul, J. Org. Chem. 1978, 43, 3170-3173.
202. K. Fukui, Orientation and Stereoselection, Springer, Berlin, 1970.
203. A. J. Heeger, Angew. Chem. 2001, 113, 2660-2682; Angew. Chem. Int. Ed. 2001, 40, 2591-2611 (Nobel lecture).
204. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, November 1998, National Institute of Standards and Technology, Gaithersburg, MD 20899 (http://webbook.nist.gov).
205. Z. B. Maksić, D. Kovaćek, M. Maksić-Eckert, M. Böckmann, M. Klessinger, J. Phys. Chem. 1995, 99, 6410-6416.
206. C. Dosche, H.-G. Löhmannsröben, A. Bieser, P. I. Dosa, S. Han, M. Iwamoto, A. Schleifenbaum, K. P. C. Vollhardt, Phys. Chem. Chem. Phys. 2002, 4, 2156-2161.
207. E. V. Shpol'skii, A. A. Il'ina, L. A. Klímova, Dokl. Akad. Nauk SSSR 1952, 87, 935-938.
208. C. Dosche, M. U. Kumke, F. Ariese, A. N. Bader, C. Gooijer, P. I. Dosa, S. Han, O. Š. Miijanić, K. P. C. Vollhardt, R. Puchta, N. J. R. Van Eikema Hommes, Phys. Chem. Chem. Phys. 2003, 5, 4563-4569.
209. C. Dosche, M. U. Kumke, H.-G. Löhmannsröben, F. Ariese, A. N. Bader, C. Gooijer, O. Š. Miijanić, M. Iwamoto, K. P. C. Vollhardt, R. Puchta, N. J. R. Van Eikema Hommes, Phys. Chem. Chem. Phys. 2004, 6, 5476-5483.
210. S. Grimme, J. Harren, A. Sobanski, F. Vögtie, Eur. J. Org. Chem. 1998, 1491-1509.
211. G. Wenz, M. A. Müller, M. Schmidt, G. Wegner, Macromolecules 1984, 17, 837-850;
212. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469; Angew. Chem. Int. Ed. 1999, 38, 1350-1377;
213. Y. Geerts, G. Kiärner, K. Müllen, in Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 1998.