Water-soluble calixarenes as new inverse phase-transfer catalysts. Nucleophilic substitution of alkyl and arylalkyl halides in aqueous media

Chemical Communications

Volumn , Issue 17, 1997, Pages 1629-1630

  Shimizu, Shoichi ^a   Kito, Katsuyuki ^a   Sasaki, Yasuyuki ^a   Hirai, Choichiro ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002574785     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704347c     Document Type: Article

References (22)

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2. For reviews, see A. Harada, J. Synth. Org. Chem. Jpn., 1990, 48, 517; Y. Goldberg, Phase Transfer Catalysis: Selected Problems and Applications. Gordon, Berkshire, 1992, pp. 359-366; C. M. Starks, C. L. Liotta and M. Halpern, Phase-Transfer Catalysis: Fundamentals. Applications, and Industrial Perspectives, Chapman, London, 1994, pp. 179-183.
3. For reviews, see A. Harada, J. Synth. Org. Chem. Jpn., 1990, 48, 517; Y. Goldberg, Phase Transfer Catalysis: Selected Problems and Applications. Gordon, Berkshire, 1992, pp. 359-366; C. M. Starks, C. L. Liotta and M. Halpern, Phase-Transfer Catalysis: Fundamentals. Applications, and Industrial Perspectives, Chapman, London, 1994, pp. 179-183.
4. For reviews, see A. Harada, J. Synth. Org. Chem. Jpn., 1990, 48, 517; Y. Goldberg, Phase Transfer Catalysis: Selected Problems and Applications. Gordon, Berkshire, 1992, pp. 359-366; C. M. Starks, C. L. Liotta and M. Halpern, Phase-Transfer Catalysis: Fundamentals. Applications, and Industrial Perspectives, Chapman, London, 1994, pp. 179-183.
5. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
6. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
7. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
8. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
9. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
10. For representative reviews, see C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and J. Böhmer, Kluwer, Dordrecht, 1991; R. M. Izatt, H. S. Bradshaw, K. Pawlak, R. L. Bruening and B. Tarbet, Chem. Rev., 1992, 92, 1261; S. Shinkai, Tetrahedron, 1993, 49, 8933; V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
11. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
12. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
13. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
14. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
15. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
16. For the use of calixarenes as normal phase transfer-catalysts, see E. Nomura, H. Taniguchi, K. Kawaguchi and Y. Otsuji, J. Org. Chem., 1993, 58, 4709; K. Araki, A. Yanagi and S. Shinkai, Tetrahedron, 1993, 49, 6763; E. Nomura, H. Taniguchi and Y. Otsuji, Bull. Chem. Soc. Jpn., 1994, 67, 309, 792; S. J. Harris, A. M. Kinahan, M. J. Meegan and R. C. Prendergast, J. Chem. Res. (S), 1994, 342; Y. Okada, Y. Sugitani, Y. Kasai and J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 586; H. Taniguchi, Y. Otsuji and E. Nomura, Bull. Chem. Soc. Jpn., 1995, 68, 3563.
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