A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions

European Journal of Organic Chemistry

Volumn , Issue 9, 2004, Pages 2002-2009

  Khan, Abu T ^a   Mondal, Ejabul ^a   Ghosh, Subrata ^a   Islam, Samimul ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

^b Department of Chemistry ^*  (India)

Author keywords

Acetals; Carbonyl compounds; Dithioacetals; Protecting groups; Solvent free reactions

Indexed keywords

ACETAL; ALCOHOL; CARBONYL DERIVATIVE; SOLVENT; THIOL DERIVATIVE;

ACETALIZATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL BOND; ROOM TEMPERATURE; SYNTHESIS;

EID: 4544289283     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300685     Document Type: Article

References (43)

1. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, Inc., New York, 1999, pp. 307-312.
2. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., John Wiley & ons, Inc., New York, 1999, pp.329-344.
3. [3a] S. D. Rychnovsky, Chem. Rev. 1995, 95, 2021-2040.
4. [3b] A. B. III Smith, S. M. Condon, J. A. McCauley, Acc. Chem. Res. 1998, 31, 35-46.
5. [4a] D. Seebach, Angew. Chem. Int. Ed. Engl. 1969, 8, 639-649.
6. [4b] B. T. Grobel, D. Seebach, Synthesis 1977, 357-402.
7. [4c] P. C. Bulman Page, M. B. van Niel, J. C. Prodger, Tetrahedron 1989, 45, 7643-7677.
8. [4d] G. R. Pettit, E. E. van Tamelen, Org. React. 1962, 12, 356.
9. M. Yus, C. Najera, F. Foubelo, Tetrahedron 2003, 59, 6147-6212.
10. [6a] V. A. Keller, J. R. Martinelli, E. R. Strieter, S. D. Burke, Org. Lett. 2002, 4, 467-470.
11. [6b] P. Wipf, J. T. Reeves, Chem. Commun. 2002, 2066-2067.
12. [7a] S. A. Patwardhan, S. Dev, Synthesis 1974, 348-349.
13. [7b] H. Firuouzabadi, N. Iranpoor, B. Karimi, Synlett 1999, 321-323.
14. [7c] B. Karimi, A. M. Ashtiani, Chem. Lett. 1999, 1199-1200.
15. [7d] B. Karimi, G. R. Ebrahimian, H. Seradj, Org. Lett. 1999, 1, 1737-1739.
16. [7e] K. Ishihara, Y. Karumi, M. Kubota, H. Yamamoto, Synlett 1996, 839-841.
17. [7f] R. Gopinath, S. J. Haque, B. K. Patel, J. Org. Chem. 2002, 67, 5842-5846.
18. H. Firouzabadi, N. Iranpoor, B. Karimi, Synthesis 1999, 58-60.
19. J. S. Yadav, B. V. S. Reddy, S. K. Pandey, Synlett 2001, 238-239.
20. S. Mathuswamy, S. Arulananda Babu, C. Gunanathan, Tetrahedron Lett. 2001, 42, 359-362.
21. S. Samajdar, M. K. Basu, F. F. Becker, B. K. Banik, Tetrahedron Lett. 2001, 42, 4425-4427.
22. A. Kamal, G. Chouhan, Synlett 2002, 474-476.
23. A. Kamal, G. Chouhan, Tetrahedron Lett. 2002, 43, 1347-1350.
24. A. T. Khan, E. Mondal, P. R. Sahu, S. Islam, Tetrahedron Lett. 2003, 44, 919-922.
25. J. H. Clark, Chemistry of Minimisation, Chapman and Hall, London, 1995.
26. [16a] E. Mondal, G. Bose, A. T. Khan, Synlett 2001, 785-786.
27. [16b] E. Mondal, G. Bose, P. R. Sahu, A. T. Khan, Chem. Lett. 2001, 1158-1159.
28. [16c] A. T. Khan, J. Boruwa, E. Mondal, G. Bose, Indian J. Chem. Sec B 2001, 40B, 1039-1042.
29. [16d] E. Mondal, P. R. Sahu, G. Bose, A. T. Khan, Tetrahedron Lett. 2002, 43, 2843-2846.
30. [16e] E. Mondal, P. R. Sahu, A. T. Khan, Synlett 2002, 463-467.
31. [16f] A. T. Khan, E. Mondal, P. R. Sahu, Synlett 2003, 377-381.
32. [17a] N. Furukawa, T. Inoue, T. Aida, S. Oae, J. Chem. Soc., Chem. Commun. 1973, 212.
33. [17b] Y. L. Chow, B. H. Bakker, Can. J. Chem. 1982, 60, 2268.
34. [17c] G. A. Olah, M. Arvanaghi, Y. D. Vankar, Synthesis 1979, 721.
35. [17d] G. A. Olah, Y. D. Vankar, M. Arvanaghi, G. K. Suraya Prakash, Synthesis 1979, 720-721.
36. A. T. Khan, E. Mondal, B. M. Borah, S. Ghosh, Eur. J. Org. Chem. 2003, 4113-4117.
37. [19a] S.-B. Lee, S.-D. Lee, T. Takata, T. Endo, Synthesis 1991, 368-370.
38. [19b] B. Bartels, R. Hunter, J. Org. Chem. 1993, 58, 6756-6765.
39. [19c] J. R. Hwu, L. Leu, J. A. Robl, D. A. Anderson, J. M. Wetzel, J. Org. Chem. 1987, 52, 188-191.
40. [19d] D. S. Torok, J. J. Figueroa, W. J. Scott, J. Org. Chem. 1993, 58, 7274-7276.
41. [19e] H. Sakurai, K. Sasaki, J. Hayashi, A. Hosomi, J. Org. Chem. 1984, 49, 2808-2809.
42. [20a] B. S. Ong, Tetrahedron Lett. 1980, 21, 4225-4228.
43. [20b] H. Firouzabadi, N. Iranpoor, H. Hazarkhani, J. Org. Chem. 2001, 66, 7527-7529.