Nuclear monobromination of alkyl phenyl ethers with NaClO2, NaBr, Mn(acac)3, and moist silica gel in aprotic solvent

Synthetic Communications

Volumn 28, Issue 8, 1998, Pages 1463-1470

  Hirano, Masao ^a   Monobe, Hiroyuki ^a   Yakabe, Shigetaka ^a   Morimoto, Takashi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYL ETHER DERIVATIVE; MANGANESE; SILICON DIOXIDE; SODIUM BROMIDE; SODIUM CHLORIDE; SOLVENT;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL WASTE; ORGANIC CHEMISTRY; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS;

EID: 0031839040     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808006845     Document Type: Article

References (41)

1. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
2. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
3. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
4. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
5. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
6. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
7. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
8. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
9. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
10. Review accounts of supported reagents are available: (a) Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents. Preparation, Analysis, and Applications; VCH: New York, 1992. (b) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994. (c) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res., 1993, 26, 607. (d) Solid Supports and Catalysts in Organic Synthesis, Smith, K. ed.; Ellis Horwood: Chichester, 1992. (e) Preparative Chemistry Using Supported Reagents, Laszlo, P. ed.; Academic Press: San Diego, 1987. (f) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993. (g) Smith, K.; Fry, C. V.; Tzimas, M. In Ref. 2(a); Ch. 4. (h) Cornelis, A.; Laszlo, P. Synthesis, 1985, 909. (i) McKillop, A.; Young, D. W. Synthesis, 1979, 401 and 481. (j) Posner, G. H. Angew. Chem., Int. Ed. Engl., 1978, 17, 487.
11. (a) Chemistry of Waste Minimization, Clark, J. H. ed.; Chapman and Hall: London, 1995. (b) Clark, J. H.; Macquarrie, D. J. Chem. Soc. Rev., 1996, 303.
12. (a) Chemistry of Waste Minimization, Clark, J. H. ed.; Chapman and Hall: London, 1995. (b) Clark, J. H.; Macquarrie, D. J. Chem. Soc. Rev., 1996, 303.
13. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
14. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
15. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
16. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
17. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
18. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
19. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
20. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
21. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
22. (a) Hirano, M.; Yakabe, S.; Monobe, H.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, in the press. (b) Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Can. J. Chem., in the press. (c) Hirano, M.; Ukawa, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (d) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis, in the press. (e) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun., 1997, 27, 2783. (f) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2693. (g) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun., 1996, 26, 1875. (h) Hirano, M.; Komiya, K.; Morimoto, T. Org. Prep. Proced. Int., 1995, 27, 703. Hirano, M.; Ueno, Y.; Morimoto, T. Synth. Commun., 1995, 25, (i) 3125 and (j) 3765.
23. (a) Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Org. Prep. Proced. Int., 1996, 28, 705. (b) Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Org. Prep. Proced. Int., 1997, 29, 480 & Synth. Commun., 1997, 27, 1527.
24. (a) Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Org. Prep. Proced. Int., 1996, 28, 705. (b) Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Org. Prep. Proced. Int., 1997, 29, 480 & Synth. Commun., 1997, 27, 1527.
25. (a) Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Org. Prep. Proced. Int., 1996, 28, 705. (b) Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Org. Prep. Proced. Int., 1997, 29, 480 & Synth. Commun., 1997, 27, 1527.
26. Surveys of structual properties of silica gels (Diddams, P. In Ref. 1 (d); Part I, Ch. 1, p. 5-8) and miscellaneous reactions with silica gel supported reagents (Ref. 1(e); Part VI) are available.
27. Butters, M. In Ref. 1(d); Part II, Ch.3, p. 76-78. Bram, G.; Loupy, A. In Ref. 1(e); Part VI, Ch. 20, p. 396-397.
28. Taylor, R. Electrophilic Aromatic Substitution; John Wiley & Sons: Chichester, 1990, Ch, 9, §9.3. March, J. Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992, p. 531-534.
29. Taylor, R. Electrophilic Aromatic Substitution; John Wiley & Sons: Chichester, 1990, Ch, 9, §9.3. March, J. Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992, p. 531-534.
30. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
31. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
32. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
33. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
34. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
35. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
36. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
37. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
38. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
39. Recently developed aromatic brominations: Smith, K.; Bahzad, D. J. Chem. Soc., Chem. Commun., 1996, 467. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439.
40. Smith, R. A. J. Am. Chem. Soc., 1933, 55, 3718.
41. Siskin, M.; Brons, G.; Katritzky, A. R.; Murugan, R. Energy Fuels, 1990, 4, 482.