Synthesis and reactions of gem-borazirconocenes

Applied Organometallic Chemistry

Volumn 10, Issue 3-4, 1996, Pages 267-278

  Zheng, Bin ^a   Deloux, Laurent ^a   Pereira, Schubert ^a   Skrzypczak Jankun, Ewa ^a   Cheesman, Bruce V ^a   Sabat, Michal ^b   Srebnik, Morris ^c  

^a UNIVERSITY OF TOLEDO   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012759520     PISSN: 02682605     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0739(199604)10:3/4<267::AID-AOC461>3.0.CO;2-D     Document Type: Review

References (119)

1. (a) A. Pelter, K. Smith and H. C. Brown, Borane Reagents, Academic Press, London, 1988.
2. (b) D. S. Matteson, in: The Chemistry of the Metal-Carbon Bond, Hartley, F. R. (ed.), Patai, S. (series ed.), Wiley, Chichester, 1987, Vol. 4, p. 307.
3. (c) B. M. Mikhailov and Y. N. Bubnov, Organoboron Compounds in Organic Synthesis, Harwood Academic, Chur, 1983.
4. (d) H. C. Brown, Organic Synthesis via Boranes, Wiley, New York, 1975.
5. (a) E. Negishi and T. Takahashi, Synthesis 1 (1988).
6. (b) J. Schwartz, G. M. Arvanitis, J. A. Smegel, I. K. Meier, S. M. Clift and D. Van Engen, Pure Appl. Chem. 60, 65 (1988).
7. (c) E. Negishi and T. Takahashi, Aldrichim. Acta 18, 31 (1985).
8. (d) U. M Dzhemilev, O. S. Vostrikova and A. G. Ibragimov, Russ. Chem. Rev. 55, 66 (1986).
9. (e) D. J. Cardin, M. F. Lappert and C. L. Raston, Chemistry of Organo-zirconium and Hafnium Compounds, Ellis Horwood, Chichester, 1986.
10. T. P. Fehlner, in Advances in Inorganic Chemistry, Academic Press, New York, 1990, Vol. 35, p. 199.
11. (a) C. A. Bertelo and J. Schwartz, J. Am. Chem. Soc. 97, 228 (1975).
12. (b) J. A. Labinger, D. W. Hart, W. E. Seibert III and J. Schwartz, J. Am. Chem. Soc. 97, 3851 (1975).
13. Ref. Id, p. 155.
14. For various references to Tebbe's reagent, see: J. March, Advanced Organic Chemistry, 5th edn, Wiley-Interscience, New York, 1992, p. 933.
15. F. W. Hartner and J. Schwartz, J. Am. Chem. Soc. 105, 640 (1983).
16. (b) S. M. Clift and J. Schwartz, J Am. Chem. Soc. 106, 8300 (1984).
17. (c) S. M. Clift and J. Schwartz, J. Organomet. Chem. 285, C5 (1985).
18. C. E. Tucker and P. Knochel, J. Am. Chem. Soc. 113, 9888 (1991).
19. I. Marek, J. Lefrancois and J. F. Normant, J. Org. Chem. 59, 4154 (1994) and references cited therein.
20. P. Knochel, J. Am. Chem. Soc. 112, 7431 (1990).
21. B. H. Lipshutz, R. Keil and J. C. Barton, Tetrahedron Lett. 33, 5861 (1992).
22. (a) A. Pelter, Pure Appl. Chem. 66, 223 (1994).
23. (b) A. Pelter, B. Singaram, L. Warren and J. W. Willson, Tetrahedron 49, 2965 (1993).
24. F. W. Hartner, Jr and J. Schwartz, J. Am. Chem. Soc. 103, 4979 (1981).
25. B. Zheng and M. Srebnik, Tetrahedron Lett. 34, 4133 (1993).
26. B. Zheng and M. Srebnik, J. Organomet. Chem. 474, 49 (1994).
27. E. Skrzypczak-Jankun, B. V. Cheesman, B. Zheng, R. M. Lemert, S. Asthana and M. Srebnik, J. Chem. Soc., Chem. Commun. 127 (1994).
28. U. Piatini, O. W. Sorenson, M. Rance and R. R. Ernst, J. Am. Chem. Soc. 104, 6800 (1982).
29. (a) A. Bax and G. A. Morris, J. Magn. Reson. 42, 510 (1981).
30. (b) V. Rutar, J. Magn. Reson. 58, 306 (1984).
31. L. Deloux, E. Skrzypczak-Jankun, B. V. Cheesman, M. Sabat and M. Srebnik, J. Am. Chem. Soc. 116, 10302 (1994).
32. J. Schwartz, Pure Appl. Chem. 52, 733 (1980).
33. J. R. Waas, A. R. Sidduri and P. Knochel, Tetrahedron Lett. 33, 3717 (1992).
34. G. Erker, R. Zwettler, C. Krüger, R. Noe and S. Werner, J. Am. Chem. Soc. 112, 9620 (1990).
35. M. Albrecht, G. Erker, M. Nolte and C. Krüger, J. Organomet. Chem. 427, C21 (1992).
36. G. Erker, M. Albrecht, C. Krüger and S. Werner, J. Am. Chem. Soc. 112, 8531 (1992).
37. A. Pelter, K. Smith, D. E. Parry and K. D. Jones, Aust. J. Chem. 45, 57 (1992).
38. T. Kusumoto, K. Nishide and T. Hiyama, Bull. Chem. Soc. Jpn. 63, 1947 (1990).
39. M. Lautens, P. H. M. Delanghe, J. B. Goh and C. H. Zhang, J. Org. Chem. 57, 3270 (1992).
40. H. C. Brown, N. G. Bhat and M. Srebnik, Tetrahedron Lett. 29, 2635 (1988).
41. R. H. Wallace and K. K. Zong, Tetrahedron Lett. 33, 6941 (1992).
42. S. L. Buchwald, S. J. LaMarie, R. B. Nielsen, B. T. Watson and S. M. King, Tetrahedron Lett. 28, 3895 (1987).
43. (a) G. C. Levy, R. L. Lichter and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd edn, Wiley, New York, 1980, p. 182.
44. (b) M. Suzuki and R. Kubo, Mol. Phys. 7, 201 (1964).
45. M. Kubo, M. Watanabe, T. Totani and M. Ohtsuru, Mol. Phys. 14, 367 (1968).
46. T. F. Blackburn, L. A. Labinger and J. Schwartz, Tetrahedron Lett. 3041 (1975).
47. H. C. Brown and K. Murray, J. Am. Chem. Soc. 81, 4108 (1959).
48. P. L. Bock, D. J. Boscherro, J. R. Rasmussen, J. R. Demers and G. M. Whitesides, J. Am. Chem. Soc. 96, 2814 (1974).
49. J. Schwartz and J. A. Labinger, Angew. Chem., Int. Ed. Engl. 15, 333 (1976).
50. H. C. Brown and M. W. Rathke, J. Am. Chem. Soc. 90, 5038 (1968).
51. H. C. Brown and C. F. Lane, J. Chem. Soc., Chem. Commun. 521 (1971).
52. (a) D. S. Matteson, Synthesis 973 (1986).
53. (b) D. S. Matteson, Tetrahedron 45, 1859 (1989).
54. (c) D. S. Matteson, Chem. Rev. 89, 1535 (1989).
55. (a) H. C. Brown, Y. Yamamoto and C. F. Lane, Synthesis 303 (1972).
56. (b) G. D. Schaumberg and S. Donovan, J. Organomet. Chem. 20, 261 (1974).
57. Y. Yamamoto and H. C. Brown, J. Org. Chem. 39, 861 (1974).
58. B. Zheng and M. Srebnik, Tetrahedron Lett. 35, 1145 (1994).
59. D. S. Matteson and J. D. Liedike, J. Am. Chem. Soc. 87, 1526 (1965).
60. H. C. Brown and R. C. Sharp, J. Am. Chem. Soc. 90, 2915 (1968).
61. D. S. Matteson and G. D. Schaumberg, J. Org. Chem. 31, 726 (1966).
62. H. C. Brown, N. G. Bhat and V. Somayaji, Organometallics 2, 1311 (1983).
63. A. E. Derome, Modern NMR Techniques for Chemistry Research, Baldwin, J. E. (ed.), Organic Chemistry Series, Pergamon, Oxford, 1987, Vol. 6, p. 169.
64. B. Zheng and M. Srebnik, Tetrahedron Lett. 35, 6247 (1994).
65. C. J. Reich, G. R. Sullivan and H. S. Mosher, Tetrahedron Lett. 1505 (1973).
66. L. Deloux and M. Srebnik, J. Org. Chem. 59, 6871 (1994).
67. (a) D. S. Matteson, H. M. Sadhu and G E. Lienhard, J. Am. Chem. Soc. 103, 5241 (1981).
68. (b) K. H. Kinder and J. A. Katzenellenbogen, J. Med. Chem. 28, 1917 (1985).
69. (c) A. B. Shenvi, Biochemistry 25, 1286 (1986).
70. T. Kelly, V. Fuchs, C. Perry and R. Snow, Tetrahedron 49, 1009 (1993).
71. Y. Tamura and J. Minamikawa, J. Org. Chem. 38, 1239 (1973).
72. J. Houben and E. Schmidt, Chem. Ber. 86, 3616 (1913).
73. M. M. Midland, S. Greer, A. Tramontano and S. Zderic, J. Am. Chem. Soc. 101, 2352 (1979).
74. B. Zheng and M. Srebnik, J. Org. chem. 60, 1912 (1995).
75. (a) For a study of the regioselectivity of hydrozirconation in various systems, see: U. Annby, S. Karlsson, S. Gronowitz, A. Hallberg, J. Alvhall and R. Svenson, Acta Chem. Scand. 47, 425 (1993).
76. 2Cl, see: S. L. Buchwald, B. T. Watson, M. W. Wannamaker and J. C. Dewan, J. Am. Chem. Soc. 111, 4486 (1989).
77. (a) G. H. Coleman, J. L. Hermanson and H. L. Johnson, J. Am. Chem. Soc. 59, 1896 (1937).
78. (b) G. H. Coleman, H. P. Andersen and J. L. Hermanson, J. Am. Chem. Soc. 56, 1381 (1934).
79. B. Zheng and M. Srebnik, unpublished results.
80. (a) E. Negishi and D. E. Van Horn, J. Am. Chem. Soc. 99, 3168 (1977).
81. (b) F. M. Dayrit, D. E Gladkowski and J. Schwartz, J. Am. Chem. Soc. 102, 3976 (1980).
82. (c) E. Negishi, T. Takahashi and D. E. Van Horn, J. Am. Chem. Soc. 109, 2393 (1987).
83. L. M. Venanzi, R. Lehman, R. Keil and B. H. Lipshutz, Tetrahedron Lett. 33, 5857 (1992).
84. (a) K. Yoshida and E. Negishi. J. Am. Chem. Soc. 103, 1276 (1981).
85. (b) T. Takahashi, T. Seki, Y. Nitto, M. Saburi, C. J. Roussel and E. Negishi, J. Am. Chem. Soc. 113, 6266 (1991).
86. P. Wipf and W. Xu, J. Org. Chem. 58, 825 (1993).
87. K. Suzuki, Pure Appl. Chem. 66, 1557 (1994).
88. B. H. Lipshutz and R. Keil, J. Am. Chem. Soc. 114, 7919 (1992).
89. (a) J. Schwartz, M. J. Loots and H. Kosugi, J. Am. Chem. Soc. 102, 1333 (1980).
90. (b) M. Loots and J. Schwartz, J. Am. Chem. Soc. 99, 8045 (1977).
91. (c) P. Wipf and J. H. Smitrovich, J. Org. Chem. 56, 6494 (1991).
92. For recent reviews, see: (a) P. Wipf, Synthesis 537 (1993). (b) P. Wipf, W. Xu, J. H. Smitravich, R. Lehmann and L. M. Venanzi, Tetrahedron 50, 1935 (1994).
93. For recent reviews, see: (a) P. Wipf, Synthesis 537 (1993). (b) P. Wipf, W. Xu, J. H. Smitravich, R. Lehmann and L. M. Venanzi, Tetrahedron 50, 1935 (1994).
94. B. Zheng and M. Srebnik, J. Org. Chem. 60, 486 (1995).
95. C. C. Tseng, S. D. Paisley and H. L. Goering, J. Org. Chem. 51, 2884 (1986).
96. For reviews, see: (a) S. Patai, The Chemistry of Ketones, Allenes, and Related Compounds, Wiley, Chichester, 1980, Part 1. (b) S. R. Landor, The Chemistry of the Allenes, Academic Press, London, 1982.
97. For reviews, see: (a) S. Patai, The Chemistry of Ketones, Allenes, and Related Compounds, Wiley, Chichester, 1980, Part 1. (b) S. R. Landor, The Chemistry of the Allenes, Academic Press, London, 1982.
98. (c) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, Wiley, New York, 1984.
99. (a) Y. Yamamoto and N. Asao, Chem. Rev. 93, 2207 (1993).
100. (b) B. M. Mikhailov and Y. N. Bubnov, Izv. Akad. SSSR, Ser. Khim. 1874 (1964).
101. (a) Y. Yamamoto, Acc. Chem. Res. 20, 243 (1987).
102. (b) R. W. Hoffman, Angew. Chem., Int. Ed. Engl. 21, 555 (1982)
103. R. W. Hoffman and T. Sander, Chem. Ber. 123, 145 (1990).
104. H. Friebolin, Basic One- and Two-Dimensional NMR Spectroscopy, 2nd edn, VCH, New York, 1993. p. 92.
105. Ref. 69c, p. 132.
106. Ref. 69b, Vol. 3, p. 681.
107. Ref. 69b, Vol. 3, p. 711.
108. M. Yoshifuji, M. J. Loots and J. Schwartz, Tetrahedron Lett. 1303 (1977).
109. (a) B. H. Lipshutz and R. Keil, Inorg. Chim. Acta 220, 41 (1994).
110. (b) B. H. Lipshutz, A. Bhandari, C. Lindsley, R. Keil and M. R. Wood, Pure Appl. Chem. 66, 1493 (1994).
111. S. Pereira and M. Srebnik, Tetrahedron Lett. 36, 1805 (1995).
112. J. J. Wright, US Patent 4 431 669 (14 February 1984); Chem. Abstr. 100, 210217k (1984).
113. M. B. Sporn, A. B. Roberts and D. S. Goodman (eds.), The Retinoids: Biology, Chemistry and Medicine, Raven Press, New York, 1994.
114. (a) W. B. Howard, C. C. Willhite and R. P. Sharma, Teratology 36, 303 (1987).
115. (b) C. C. Willhite and M. I. Dawson, Toxicol. Appl. Pharmacol. 103, 324 (1990).
116. M. I. Dawson, P D. Hobbs, K. A. Derdzinski, W.-R. Chao, G. Frenking, G. H. Loew, A. M. Jetten, J. L. Napoli, J. B. Williams, B. P. Sani, J. J. Wille, Jr. and L. J. Schiff, J. Med. Chem. 32, 1504 (1989).
117. For the synthesis of related compounds, see: (a) W. Hanefeld and M. Jung, Liebigs Ann. Chem. 59 (1994). (b) W. Hanefeld and M. Jung, Liebigs Ann. Chem. 331 (1994).
118. For the synthesis of related compounds, see: (a) W. Hanefeld and M. Jung, Liebigs Ann. Chem. 59 (1994). (b) W. Hanefeld and M. Jung, Liebigs Ann. Chem. 331 (1994).
119. L. Deloux and M. Srebnik, J. Org. Chem. 60, 3276 (1995).