A green chemical approach for the N-alkylation of aldoximes to form nitrones in organized aqueous media and their in situ cycloaddition with olefins

Green Chemistry

Volumn 11, Issue 2, 2009, Pages 169-17

  Hota, Sandip K ^a   Chatterjee, Amrita ^a   Bhattacharya, Pranab K ^a   Chattopadhyay, Partha ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67649432936     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b812290c     Document Type: Article

References (52)

1. P. Anastas, L. G. Heine, T. C. Williamson, in Green Chemical Syntheses and Processes, Oxford University Press, New York, 2000.
2. M. Lancaster, in Green Chemistry: An Introductory Text, Royal Society of Chemistry, Cambridge, UK, 2002.
3. I. T. Horvath Acc. Chem. Res. 2002 35 685-685.
4. J. Andraos Org. Process Res. Dev. 2005 9 149-163.
5. A. S. Matlack, Introduction to Green Chemistry, Marcel Dekker, New York, NY, 2001.
6. M. Lancaster, in Handbook of Green Chemistry and Technology, ed. J. H. Clark, D. J. Macquarrie, Blackwell Publishing, Abingdon, 2002.
7. P. T. Anastas M. M. Kirchhoff Acc. Chem. Res. 2002 35 686-694.
8. Green Chemistry: Theory and Practice, ed. P. T. Anastas, J. C. Warner, Oxford University Press, Oxford, UK, 1998.
9. U. S. Environmental Protection Agency, http://www.epa.gov/greenchemistry/principles.html.
10. U. M. Lindstrom, Organic Recations in Water: Principles, Strategies and Application, Blackwell Publishing, Abingdon, 2007 and references cited therein.
11. J. B. F. N. Engberts M. J. Blandamer Chem. Commun. 2001 1701-1708.
12. U. M. Lindstrom Chem. Rev. 2002 102 2751-2772.
13. M. C. Pirrung K. Das Sarma J. Am. Chem. Soc. 2004 126 444-445.
14. D. Dallinger C. O. Kappe Chem. Rev. 2007 107 2563-2591 and references cited therein.
15. C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997.
16. C.-J. Li Chem. Rev. 2005 105 3095-3166.
17. Organic Synthesis in Water, ed. P. A. Grieco, Blackie Academic and Professional, England, 1998.
18. Y. Kita H. Nambu N. G. Ramesh G. Anilkumar M. Matsugi Org. Lett. 2001 3 1157-1160.
19. T. Okino Y. Takemoto Org. Lett. 2001 3 1515-1517.
20. K. Manabe S. Iimura X.-M. Sun S. Kobayashi J. Am. Chem. Soc. 2002 124 11971-11978.
21. A. Chatterjee D. K. Maiti P. K. Bhattacharya Org. Lett. 2003 5 3967-3969.
22. A. Chatterjee P. K. Bhattacharya J. Org. Chem. 2006 71 345-348.
23. We performed the dynamic light scattering (DLS) study and observed that the surfactant in aqueous solution is self-assembled to form the nanoreactor, with hydrodynamic radii of 1.167 nm (27.65%) and 97.75 nm (72.35%).
24. D. M. Vriezema M. Comellas Aragones J. A. A. W. Elemans J. J. L. M. Cornelissen A. E. Rowan R. J. M. Nolte Chem. Rev. 2005 105 1445-1490.
25. M. Lee C.-J. Jang J.-H. Ryu J. Am. Chem. Soc. 2004 126 8082-8083.
26. For the generation of nitrones by N-alkylation of aldoximes in non-aqueous media, see: K. Nakama S. Seki S. Kanemasa Tetrahedron Lett. 2001 42 6719-6722.
27. A. Padwa Angew. Chem., Int. Ed. Engl. 1976 15 123-136.
28. W. Oppolzer Angew. Chem., Int. Ed. Engl. 1977 16 10-23.
29. C. P. Dell J. Chem. Soc., Perkin Trans. 1 1998 3873-3905.
30. M. Lombardo C. Trombini Synthesis 2000 6 759.
31. K. V. Gothelf K. A. Jorgensen Chem. Rev. 1998 98 863-910.
32. S. Kanemasa T. Tsuruoka H. Yamamoto Tetrahedron Lett. 1995 36 5019-5022.
33. A. Padwa, in New Synthetic Methods, Verlag Chemie, New York, 1979, vol. 5.
34. M. A. Voinov I. A. Grigorev Tetrahedron Lett. 2002 43 2445-2447.
35. R. Alibes P. Blanco P. March M. Figueredo J. Font A. Alvarez-Larena J. F. Piniella Tetrahedron Lett. 2003 44 523-525.
36. 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984, vol. 2, ch. 9, pp. 83–168.
37. M. Noguchi H. Okada S. Nishimura Y. Yamagata S. Takamura M. Tanaka A. Kakehi H. Yamamoto J. Chem. Soc., Perkin Trans. 1 1999 185-192.
38. H. Miyabe K. Yoshida V. K. Reddy A. Matsumura Y. Takemoto J. Org. Chem. 2005 70 5630-5635.
39. H. A. Dondas C. W. G. Fishwick R. Grigg M. Thornton-Pett Tetrahedron 2003 59 9997-10007 and references cited therein.
40. S. E. Denmark A. Thorarensen Chem. Rev. 1996 96 137-166.
41. R. Grigg Chem. Soc. Rev. 1987 16 89-121 and references cited therein.
42. D. Francois A. Maden W. V. Murray Org. Lett. 2004 6 1931-1934.
43. R. Grigg F. Heaney J. Markandu S. Surendrakumar T.-P. Mark W. J. William Tetrahedron 1991 47 4007-4030.
44. A. Hassner R. Maurya O. Friedman H. E. Gottlieb A. Padwa D. Austin J. Org. Chem. 1993 58 4539-4546.
45. P. Armstrong R. Grigg W. J. Warnock J. Chem. Soc., Chem. Commun. 1987 1325-1327.
46. R. Grigg J. F. Malone M. J. Dorrity F. Heaney S. Rajviroongit V. Sridharan S. Surendrakumar Tetrahedron Lett. 1988 29 4323-4324.
47. R. Grigg M. J. Dorrity F. Heaney J. F. Malone S. Rajviroongit V. Sridharan S. Surendrakumar Tetrahedron 1991 47 8297-8322.
48. M. T. McKiernan F. Heaney Tetrahedron Lett. 1996 37 4597-4600.
49. 2 using SHELXL-97.17 Non-hydrogen atoms were refined with anisotropic thermal parameters. The final R value was R1 = 0.0456 and wR2 = 0.1500 with I > 2σ(I). Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre with reference numbers CCDC 686184.
50. G. M. Sheldrick, SHELXS-97, Program for solution of crystal structures, University of Göttingen, Germany, 1997.
51. G. M. Sheldrick Acta Crystallogr. A 1990 46 467-473.
52. G. M. Sheldrick, SHELXL-97, Program for refinement of crystal structures, University of Göttingen, Germany, 1997.