Directed ortho metalation of ferrocenes. Ring-substituted fulvenes by Nesmeyanov ferrocenylcarbenium ion fragmentation

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2449-2452

  Miao, Bing ^a   Tinkl, Michael ^a   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; FERROCENE DERIVATIVE; FULVENE DERIVATIVE; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033605799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00246-4     Document Type: Article

References (34)

1. a) Taken, in part, from the M.Sc. Thesis of Miao, B. University of Waterloo, 1998.
2. b) Present address: Additives Research, CIBA, 180.154, CH-1723 Marly, Switzerland.
3. c) Present address: Department of Chemistry, Queen's Univeristy, Kingston, ON, Canada K7L 3N6, Fax: 613-544-2837, email: baderadm@chem.queensu.ca.
4. Thiele, J. Chem. Ber. 1990, 33, 666.
5. Carey F. A.; Sundberg R. J. Advanced Organic Chemistry, 3rd Ed. Part A, Plenum, New York, 1990, pp 528-530. For a witty account, see Nickon, A.; Silversmith, E. F. Organic Chemistry: The Name Game, Pergamon Press, New York, 1987, p 287.
6. Carey F. A.; Sundberg R. J. Advanced Organic Chemistry, 3rd Ed. Part A, Plenum, New York, 1990, pp 528-530. For a witty account, see Nickon, A.; Silversmith, E. F. Organic Chemistry: The Name Game, Pergamon Press, New York, 1987, p 287.
7. For reviews, see a) Bergmann, E. D. Chem. Rev. 1968, 68, 41-84.
8. b) Zeller, K. P. Houben-Weyl: Methoden der Organischen Chemie; 1985, Vol.5/2C, p 504-684.
9. c) Neuenschwander, M. InThe Chemistry of Double-Bonded Functional Groups; Suppl. A. Patai, S. Ed.; Wiley, New York, 1989, p 1131-1268.
10. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett.1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
11. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
12. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
13. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
14. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
15. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
16. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
17. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
18. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.;Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
19. For leading references, see Büchi, G.; Berthet, D.; Decorzant R.; Grieder, A.; Hauser. A. J. Org. Chem. 1976. 41, 3208. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928. Nyström, J. -E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. Sternbach, D. D.; Ensinger, C. L. J. Org. Chem. 1990, 55, 2725. Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990. 55, 4504. Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609. Sîderberg, B. C.; Austin, L. R.; Davis, C. A.; Nystîm, J. -E.; Vügberg, J. O. Tetrahedron 1994, 50, 61. Rawal, V. H.; Fabré, A.; Iwasa, S. Tetrahedron Lett. 1995, 36, 6851. For the synthesis of natural and unnatural fulvenoid terpenes, see McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 1997, 62, 3015 and McMorris, T.C.; Hu, Y; Yu, J.; Kelner, M.J. J. Chem. Soc., Chem. Commun. 1997, 315.
20. Watts, W. E. J. Organometal. Chem. Libr. 1979, 7, 399.
21. a) Nesmeyanov, A. N.; Sazonova, V. A.; Drozd, V. N. Doklady Akad. Nauk SSSR, 1964, 154, 1393; Chem. Abstr. 1964, 60, 11937d.
22. a) Nesmeyanov, A. N.; Sazonova, V. A.; Drozd, V. N. Doklady Akad. Nauk SSSR, 1964, 154, 1393; Chem. Abstr. 1964, 60, 11937d.
23. b) Nesmeyanov, A. N.; Sazonova, V. A.; Drozd, V. N.; Rodinova, N. A. Doklady Akad. Nauk SSSR, 1965, 160, 355, Engl. Edit., p 62; Chem. Abstr. 1965, 62, 14725b.
24. b) Nesmeyanov, A. N.; Sazonova, V. A.; Drozd, V. N.; Rodinova, N. A.Doklady Akad. Nauk SSSR, 1965, 160, 355, Engl. Edit., p 62; Chem. Abstr. 1965, 62, 14725b.
25. c) Nesmeyanov, A. N.; Sazonova, V. A.; Zudkova, G. I.; Isaeva, L. S. Isz. Akad. Nauk SSSR, Ser. Chim. 1966, 2017, Engl. Edit. p 1949, Chem. Abstr. 1967, 66, 76133d.
26. c)Nesmeyanov, A. N.; Sazonova, V. A.; Zudkova, G. I.; Isaeva, L. S. Isz. Akad. Nauk SSSR, Ser. Chim.1966, 2017, Engl. Edit. p 1949, Chem. Abstr. 1967, 66, 76133d.
27. For ring unsubstituted fulvenes, the prominent methods are: a) base-mediated condensation of cyclopentadienes with carbonyl compounds (Thiele reaction): Little, R. D.; Stone, K. J. J. Org. Chem. 1984, 49, 1849 and extensive citations therein. For a modification and synthesis of vinylfulvenes, see Erden, I.; Xu, F. -P.; Sadoun, A.; Smith, W.; Sheff, G.; Ossun, M. J. Org. Chem. 1995, 60, 813;
28. For ring unsubstituted fulvenes, the prominent methods are: a) base-mediated condensation ofcyclopentadienes with carbonyl compounds (Thiele reaction): Little, R. D.; Stone, K. J. J. Org. Chem. 1984, 49, 1849 and extensive citations therein. For a modification and synthesis of vinylfulvenes, see Erden, I.; Xu, F. -P.; Sadoun, A.; Smith, W.; Sheff, G.; Ossun, M. J. Org. Chem. 1995, 60, 813;
29. b) electrophilic substitution, Straud, P. A.; Meuche, D.; Heilbronner, E. Helv. Chim. Acta 1966, 49, 517.
30. d) photochemical method of potential greater value, Nesmeyanov, A. N.; Sazonova, V. A.; Gerasimenko A. V.; Sazonova, N. S. Doklady Akad. Nauk SSSR, 1963, 149, 1354, Engl. Edit. p. 376, Chem. Abstr. 1963, 59, 3460h.
31. d) photochemicalmethod of potential greater value, Nesmeyanov, A. N.; Sazonova, V. A.; Gerasimenko A. V.; Sazonova, N.S. Doklady Akad. Nauk SSSR, 1963, 149, 1354, Engl. Edit. p. 376, Chem. Abstr. 1963, 59, 3460h.
32. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685.
33. Synthesis of the ferrocenyl phosphine oxide precursor: Chapell, B. J.; Snieckus, V. unpublished results.
34. Laufer, R. M.sc. thesis, University of Waterloo, 1998.