π Complexes with annellated cyclobutene rings: Bicyclo[3.2.0]heptadienyl Anion and benzocyclobutene as ligands for transition metals

Synlett

Volumn , Issue 6, 1999, Pages 680-691

  Butenschön, Holger ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Benzocyclobutene complexes; Bicyclo 3.2.0 heptadienyl complexes; Chromium; Cobalt; Dianionic oxy Cope rearrangement

Indexed keywords

BENZOCYCLOBUTENE COMPLEX; BICYCLO[3.2.0]HEPTADIENYL COBALT COMPLEX; CYCLOBUTANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DIASTEREOISOMER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033038574     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2700     Document Type: Article

References (104)

1. O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307-318.
2. Oda, M.; Breslow, R. Tetrahedron Lett. 1973, 2537-2540.
3. Borden, G. W.; Chapman, O. L.; Swindell, R.; Tezuka, T. J. Am. Chem. Soc. 1967, 89, 2979-2986.
4. Lehmkuhl, H.; Leuchte, H. W.; Janssen, E. J. Organomet. Chem. 1971, 30, 407-409.
5. Leuchte, H. W. Dissertation, Ruhr-Universität Bochum 1971.
6. Otsuka, S.; Taketomi, T. J. Chem. Soc., Dalton Trans. 1972, 1879-1882.
7. Butenschön, H.; Betz, P. J. Chem. Soc., Chem. Commun. 1990, 500-501.
8. Angermund, K. P.; Betz, P.; Butenschön, H. Chem. Ber. 1993, 126, 713-724.
9. Butenschön, H. J. Chem. Soc., Perkin Trans. 1 1991, 483-484.
10. Butenschön, H. Chem. Ber. 1994, 127, 137-144.
11. Behrendt, U.; Gabor, B.; Mynott, R.; Butenschön, H. Liebigs Ann. 1996, 1167-1173.
12. Butenschön, H. Angew. Chem. 1990, 102, A-296.
13. Butenschön, H. Angew. Chem. 1990, 102, 1058-1059.
14. Butenschön, H. Chem. Ber. 1993, 126, 1651-1656.
15. Iyoda, M.; Sultana, F.; Sasaki, S.; Butenschön, H. Tetrahedron Lett. 1995, 36, 579-582.
16. Trahanovsky, W. S.; Ferguson, J. M. Organometallics 1992, 11, 2006-2007.
17. Klundt, I. L. Chem. Rev. 1970, 70, 471-487.
18. Oppolzer, W. Angew. Chem. 1977, 89, 10-24.
19. Oppolzer, W. Synthesis 1978, 793-802.
20. Thummel, R. P. Acc. Chem. Res. 1980, 13, 70-76.
21. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61.
22. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
23. Fishwick, C. W. G.; Jones, D. W. ortho-Quinonoid compounds; Fishwick, C. W. G.; Jones, D. W., Ed.; Wiley: New York, 1988, pp 403-453.
24. Boese, R. Chem. Unserer Zeit 1989, 23, 77-85.
25. Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Int. 1991, 25, 139-272.
26. Griesbeck, A. G. J. Prakt. Chem. Chem. Ztg. 1993, 335, 489-502.
27. Dolbier Jr., W. R.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471-477.
28. Nemoto, H.; Fukumoto, K. Tetrahedron 1998, 54, 5425-5464.
29. Kametani, T.; Fukumoto, K. Acc. Chem. Res. 1976, 9, 319-325.
30. Kametani, T.; Honda, T.; Ebisawa, Y.; Ichikawa, H. Tetrahedron 1985, 41, 3643-3653.
31. Eckert-Maksic, M.; Kovacek, D.; Hodoscek, M.; Mitic, D.; Poljanec, K.; Maksic, Z. B. J. Molec. Struct. 1990, 206, 89-98.
32. Kündig, E. P.; Grivet, C.; Wenger, E.; Bernardinelli, G.; Williams, A. F. Helv. Chim. Acta 1991, 74, 2009-2023.
33. Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 9583-9587.
34. Eckert-Maksic, M.; Maksic, Z. B.; Hodoscek, M.; Poljanec, K. J. Molec. Struct. 1993, 285, 187-194.
35. Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1993, 115, 11153-11157.
36. Eckert-Maksic, M.; Maksic, Z. B.; Klessinger, M. J. Chem. Soc., Perkin Trans. 2 1994, 285-289.
37. Siegel, J. S. Angew. Chem. 1994, 106, 1808-1810.
38. Mitchell, R. H.; Chen, Y.; Iyer, V. S.; Lau, D. Y. K.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1996, 118, 2907-2911.
39. Illescas, B. M.; Martín, N.; Seoane, C.; Ortí, E.; Viruela, P. M.; Viruela, R.; de la Hoz, A. J. Org. Chem. 1997, 62, 7585-7591.
40. Baldridge, K. K.; Kasahara, Y.; Ogawa, K.; Siegel, J. S.; Tanaka, K.; Toda, F. J. Am. Chem. Soc. 1998, 120, 6167-6168.
41. Bettinger, H. F.; Schleyer, P. v. R.; Schacfer III, H. F. Chem. Commun. 1998, 769-770.
42. Elschenbroich, C.; Koch, J.; Schneider, J.; Spangenberg, B.; Schiess, P. J. Organomet. Chem. 1986, 317, 41-54.
43. Wey, H. G. Dissertation, Ruhr-Universität Bochum 1990.
44. Gracey, D. E. F.; Jackson, W. R.; Jennings, W. B.; Rennison, S. C.; Spratt, R. J. Chem. Soc. B 1969, 1210-1214.
45. Wey, H. G.; Butenschön, H. J. Organomet. Chem. 1988, 350, C8-C12.
46. Wey, H. G.; Betz, P.; Butenschön, H. Chem. Ber. 1991, 124, 465-474.
47. Kündig, E. P.; Perret, C.; Spichiger, S.; Bernardinelli, G. J. Organomet. Chem. 1985, 286, 183-200.
48. Kündig, E. P.; Leresche, J.; Saudan, L.; Bernardinelli, G. Tetrahedron 1996, 52, 7363-7378.
49. Kündig, E. P.; Leresche, J. Tetrahedron 1993, 49, 5599-5615.
50. Schmidt, T. Dissertation, Universität zu Köln 1986.
51. Wey, H. G., Betz, P.; Topalovic, I.; Butenschön, H. J. Organomet. Chem. 1991, 411, 369-374.
52. Ashkenazi, N. Ph. D. thesis, Technion - Israel Institute of Technology 1997.
53. Kündig, E. P.; Bernardinelli, G.; Leresche, J.; Romanens, P. Angew. Chem. 1990, 102, 421-423.
54. Semmelhack, M. F.; Sufert, W.; Keller, L. J. Organomet. Chem. 1982, 226, 183-190.
55. Kündig, E. P.; Kontratenko, M.; Romanens, P. Angew. Chem. 1998, 110, 3329-3332.
56. Leong, V. S.; Cooper, N. J. J. Am. Chem. Soc. 1988, 110, 2644-2646.
57. Horner, L.; Subramaniam, P. V.; Eiben, K. Liebigs Ann. Chem. 1968, 714, 91-111.
58. Choy, W.; Yang, H. J. Org. Chem. 1988, 53, 5796-5798.
59. Wey, H. G.; Butenschön, H. Angew. Chem. 1991, 103, 871-873.
60. Brands, M.; Wey, H. G.; Krömer, R.; Krüger, C.; Butenschön, H. Liebigs Ann. 1995, 253-265.
61. Jefford, C. W.; Bernardinelli, G.; Wang, Y.; Spellmeyer, D. C.; Buda, A.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1157-1165.
62. Kündig, E. P.; Leresche, J. E.; Bernardinelli, G. Sixth IUPAC Symposium on Organo-Metallic Chemistry Directed Towards Organic Synthesis, Utrecht, The Netherlands 1991, IUPAC, University of Utrecht, C65.
63. Kündig, E. P.; Bernardinelli, G.; Leresche, J. J. Chem. Soc., Chem. Commun. 1991, 1713-1715.
64. Davies, S. G.; Goodfellow, C. L. Synlett 1989, 59-62.
65. Brands, M.; Wey, H. G.; Butenschön, H. J. Chem. Soc., Chem. Commun. 1991, 1541-1542.
66. Brands, M.; Wey, H. G.; Goddard, R.; Butenschön, H. Inorg. Chim. Acta 1994, 220, 175-186.
67. Solladié-Cavallo, A.; Solladié, G.; Tsamo, E. J. Org. Chem. 1979, 44, 4189-4191.
68. Solladié-Cavallo, A.; Solladié, G.; Tsamo, E. Inorg. Synth. 1985, 23, 85-90.
69. Brands, M.; Plaschke, H.; Butenschön, H., unpublished results.
70. Schmalz, H.-G.; Millies, B.; Bats, J. W.; Dürner, G. Angew. Chem. 1992, 104, 640-643.
71. Butenschön, H.; Brands, M.; Wey, H. G. Sixth IUPAC Symposium on Organo-Metallic Chemistry Directed Towards Organic Synthesis, Utrecht, The Netherlands 1991, IUPAC, University of Utrecht, C5.
72. Yoon, T.; Danifshefsky, S. J.; de Gala, S. Angew. Chem. 1994, 106, 923-925.
73. Charlton, J. L.; Koh, K.; Plourde, G. L. Tetrahedron Lett. 1989, 30, 3279-3282.
74. Charlton, J. L.; Plourde, G. L.; Koh, K.; Seco, A. S. Can. J. Chem. 1989, 67, 574-579.
75. Charlton, J. L.; Maddaford, S.; Koh, K.; Boulet, S.; Saunders, M. H. Tetrahedron: Asymmetry 1993, 4, 645-648.
76. Charlton, J. L.; Koh, K. Synlett 1990, 333-334.
77. Yalpani, M.; Benn, R.; Goddard, R.; Wilke, G. J. Organomet. Chem. 1982, 240, 49-57.
78. Ziehe, H. Dissertation, Universität Hannover 1998.
79. Brands, M.; Goddard, R.; Wey, H. G.; Butenschön, H. Angew. Chem. 1993, 105, 285-287.
80. Leinweber, D.; Butenschön, H. Tetrahedron Lett. 1997, 38, 6385-6386.
81. Mills, W. H.; Nixon, I. G. J. Chem. Soc. 1930, 2510-2524.
82. Stanger, A. J. Am. Chem. Soc. 1991, 113, 8277-8280.
83. Mó O.; Yanez, M.; Eckert-Maksic, M.; Maksic, Z. B. J. Org. Chem. 1995, 60, 1638-1646.
84. Cardullo, F.; Giuffrida, D.; Kohnke, F. H.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. Angew. Chem. 1996, 108, 347-349.
85. Stanger, A.; Boese, R.; Ashkenazi, N.; Stellberg, P. J. Organomet. Chem. 1997, 542, 19-24.
86. Stanger, A.; Ashkenazi, N.; Boese, R. J. Org. Chem. 1998, 63, 247-253.
87. Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012-6018.
88. Butenschön, H.; Gabor, B.; Mynott, R.; Wey, H. G. Z. Naturforsch. B 1995, 50b, 483-487.
89. Maier, G.; Reisenauer, H. P.; Röther, B.; Eckwert, J. Liebigs Ann. 1996, 303-306.
90. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058.
91. Bennett, M. A.; Sehwemlein, H. P. Angew. Chem. 1989, 101, 1349-1373.
92. Bennett, M. A.; Wenger, E. Chem. Ber. 1997, 130, 1029-1042.
93. Wittneben, D.; Grützmacher, H.-F.; Butenschön, H.; Wey, H. G. Organometallics 1992, 11, 3111-3116.
94. Schröder, E. Massenspektrometrie - Begriffe und Definitionen; Springer-Verlag: Berlin, 1991.
95. Budzikiewicz, H. Massenspektrometrie; 4th ed.; Wiley-VCH: Weinhcim, 1998.
96. Pyrek, J. S. Synlett 1999, 249-266.
97. Palomino, E.; Schaap, A. P.; Heeg, M. J. Tetrahedron Lett. 1989, 30, 6797-6800.
98. Barnier, J. P.; Ollivier, J.; Salaün, J. Tetrahedron Lett. 1989, 30, 2525-2528.
99. Brands, M.; Brackmann, J.; Krüger, C.; Butenschön, H. J. Chem. Soc., Chem. Commun. 1994, 999-1000.
100. Brands, M.; Wey, H. G.; Brackmann, J.; Krüger, C.; Butenschön, H. Chem. Eur. J. 1996, 2, 182-190.
101. Voigt, B.; Brands, M.; Goddard, R.; Wartchow, R.; Butenschön, H. Eur, J. Org. Chem, 1998, 2719-2727.
102. Clausen, C. Dissertation, Universität Hannover 1998.
103. Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189-12190.
104. Paquette, L. A. Tetrahedron 1997, 53, 13971-14020.