Nitrilimine cycloadditions in aqueous media

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 22, 2000, Pages 3742-3745

  Molteni, Giorgio ^a   Orlandi, Marco ^b   Broggini, Gianluigi ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; SOLUBILITY; SOLUTIONS; SURFACE ACTIVE AGENTS;

CYCLOADDITIONS;

AMINES;

EID: 0034700399     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005567k     Document Type: Article

References (38)

1. (a) Organic Synthesis in Water, ed. P. A. Grieco, Blackie, Glasgow, 1998;
2. (b) A. Lubineau, Chim. Ind. (London), 1996, 123;
3. (c) A. Lubineau; J. Augé and Y. Queneau, Synthesis, 1994, 741;
4. (d) C.-J. Li, Chem. Rev., 1993, 93, 2023;
5. (e) R. Breslow, Acc. Chm Res., 1991, 24, 159;
6. (f) P. A. Grieco, Aldrichimica Acta, 1991, 24, 59.
7. R. Breslow, U. Maitra and D. C. Rideout, Tetrahedron Lett., 1983, 24, 1901;
8. (b) L. A. Van Royen, R. Mijngheer and P. J. De Clercq, Tetrahedron, 1985, 41, 4667;
9. (c) H. Waldmann, Angew. Chem., Int. Ed. Engl., 1988, 27, 274;
10. (d) H. Waldmann and M. Braun, Liebigs Ann. Chem., 1991, 1045;
11. (e) W. Blokzijl, M. J. Blandamer and J. B. F. N. Engberts, J. Am. Chem. Soc., 1991, 113, 4241;
12. (f) J. W. Wijnen and J. B. F. N. Engberts, J. Org. Chem., 1997, 62, 2039.
13. R. Huisgen, Angew. Chem., Int. Ed Engl., 1963, 2, 633.
14. D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816.
15. (a) C. Grundmann and R. Richter, J. Org. Chem., 1967, 32, 2308;
16. (b) C. Grundmann and S. K. Datta, J. Org. Chem., 1969, 34, 2016.
17. (a) K. J. Dignam, A. F. Hegarty and P. L. Quain, J. Org. Chem., 1978, 43, 388;
18. (b) Y. Inoue, K. Araki and S. Shiraishi, Bull. Chem. Soc. Jpn., 1991, 64, 3079;
19. (c) J. C. Rohloff, J. Robinson and J. O. Gardner, Tetrahedron Lett., 1992, 33, 3113;
20. (d) D. van Mersbergen, J. W. Wijnen and J. B. F. N. Engberts, J. Org. Chem., 1998, 63, 8801.
21. (a) R. Grigg, T. Mongkolaussavaratana, C. A. Pounds and S. Sivagnanam, Tetrahedron Lett., 1990, 31, 7215;
22. (b) A. Lubineau, G. Bouchain and Y. Queneau, J. Chem. Soc., Perkin Trans. 1, 1995, 2433.
23. J. W. Wijnen, R. A. Steiner and J. B. F. N. Engberts, Tetrahedron Lett., 1995, 36, 5389.
24. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley-Interscience, New York, 1984, vol. 1, ch. 1.
25. (a) G. Bianchi, C. De Micheli and R. Gandolfi, in The Chemistry of Double Bonded Functional Groups, ed. S. Patai, Wiley, London, 1977, part I, ch. 6;
26. (b) P. Caramella and P. Grünanger, in 1.3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley-Interscience, New York, 1984, vol. 1. ch. 3.
27. (a) A. S. Shawali and C. Párkáni, J. Heterocycl. Chem., 1980, 17, 833;
28. (b) P. K. Claus, in Methoden der Organishe Chemie (Houben-Weil), eds. D. Klamann and H. Hagemann, Georg Thieme Verlag, Stuttgart, 1990, Band E14b, Teil 1, p. 33.
29. (a) R. Paul and S. Tchelitcheff, Bull. Soc. Chim. Fr., 1967, 4179;
30. (b) T. Shimizu, Y. Hayashi, T. Nishio and K. Teramura, Bull. Chem. Soc. Jpn., 1984, 57, 787;
31. (c) A. S. Shawali and S. T. Ezmirly, J. Heterocycl. Chem., 1988, 25, 257.
32. (a) C. A. Bunton and G. Savelli, Adv. Phys. Org. Chem., 1986, 22, 213;
33. (b) C. A. Bunton, F. Nome, F. H. Quina and L. S. Romsted, Acc. Chem. Res., 1991, 24, 357.
34. F. Fringuelli, O. Piermatti and F. Pizzo, Targets in Heterocyclic Systems, Springer, Heidelberg, 1997, vol. 1, p. 57.
35. (a) K. N. Houk, J. Sims, R. E. Duke, R. W Strozier and J. K. George, J. Am. Chem. Soc., 1973, 95, 7287;
36. (b) K. N. Houk, J. Sims, C. R. Watts and L. J. Luskus, J. Am. Chem. Soc., 1973, 95, 7301;
37. (c) K. N. Houk and P. Caramella, J. Am. Chem. Soc., 1976, 98, 6397.
38. M. M. El-Abadelah, A. Q. Hussein, M. R. Kamal and K. H. Al-Adhami, Heterocycles, 1988, 27, 917.