Unusual radical ipso-substitution reaction of an aromatic methoxy group induced by tris(trimethylsilyl)silane-AIBN or SmI2

Chemical Communications

Volumn , Issue 14, 2000, Pages 1287-1288

  Tanaka, Tetsuaki ^a   Wakayama, Ryutaro ^a   Maeda, Shin ichiro ^a   Mikamiyama, Hidenori ^a   Maezaki, Naoyoshi ^a   Ohno, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; THIOCARBAMIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION;

EID: 0034698399     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003742g     Document Type: Article

References (22)

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10. Demethoxylative C-C bond formation is known to occur in very limited cases, see: W. S. Lee, I.-Y. Jeong, M. Shiro, S. Sano and Y. Nagao, Tetrahedron Lett., 1997, 38, 611 ; R. Yanada, N. Negoro, M. Okaniwa, Y. Miwa, T. Taga, K. Yanada and T. Fujita, Synlett, 1999, 537; for C-O bond formation, see: K. Nowada, H. Sakuragi, K. Tokumaru and M. Yoshida, Chem. Lett., 1976, 1243.
11. Demethoxylative C-C bond formation is known to occur in very limited cases, see: W. S. Lee, I.-Y. Jeong, M. Shiro, S. Sano and Y. Nagao, Tetrahedron Lett., 1997, 38, 611 ; R. Yanada, N. Negoro, M. Okaniwa, Y. Miwa, T. Taga, K. Yanada and T. Fujita, Synlett, 1999, 537; for C-O bond formation, see: K. Nowada, H. Sakuragi, K. Tokumaru and M. Yoshida, Chem. Lett., 1976, 1243.
12. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
13. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
14. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
15. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
16. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
17. For related works, see: H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383; O. Hoffmann and H.-G. Schmalz, Synlett, 1998, 1426; C. U. Dinesh and H.-U. Reissig, Angew. Chem., Int. Ed., 1999, 38, 789; D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765; J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1997, 38, 5988; A. Citterio, R. Sebastiano, A. Maronati, R. Santi and F. Bergamini, J. Chem. Soc., Chem. Commun., 1994, 1517.
18. MD and MO calculations were performed by SPARTAN (Ver. 5.1.1) using MM 2 method and PM 3 Hamiltonian.
19. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693; G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
20. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693; G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
21. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693; G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
22. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693; G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.