Highly efficient transdithioacetalization of acetals catalyzed by silica chloride

Synlett

Volumn , Issue 2, 2000, Pages 263-265

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Karimi, Babak ^b   Hazarkhani, Hassan ^a  

^a SHIRAZ UNIVERSITY   (Iran)

^b INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Acetals; Protection; Silica chloride; Thioacetals; Transdithioacetalization

Indexed keywords

ACETAL; CHLORIDE; SILICON DIOXIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033964187     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6483     Document Type: Article

References (37)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York 1991, pp 178-207.
2. (a) Corey, E. J.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1965, 4, 1075, 1077.
3. (b) Seebach, D. Angew. Chem. Int. Ed. Engl. 1969, 8, 639.
4. (c) Grobel, B. T.; Seebach, D. Synthesis 1977, 357.
5. (d) Bulman Page, P. C.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643.
6. Pettit, G. R.; Van Tamelen, E. E. Org. React. 1962, 12, 356.
7. (a) Garlaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31, 5815.
8. (b) Hauptmann, H.; Moura Campos, M. J. Am. Chem. Soc. 1950, 72, 1405.
9. (c) Seebach, D.; Kolb, M. Chem. Ind. (London) 1974, 687.
10. (d) Ong, B. S. Tetrahedron Lett. 1980, 4225.
11. (e) Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24, 1289.
12. (f) Ku, B.; Oh, D. Y. Synth. Commun. 1989, 19, 433.
13. (g) Ong, B. S.; Chan, T. H. Synth. Commun. 1977, 7, 283.
14. (h) Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169.
15. (i) Chowdhury, P. K. J. Chem. Res.(Synop) 1993, 124.
16. (j) Das, N. B.; Nayak, A.; Sharma, R. P. J. Chem. Res. (Synop) 1993, 242.
17. (k) Komatsu, N.; Uda, M.; Suzuki, H. Synlett 1995, 984.
18. (a) Kumar, P.; Reddy, R. S.; Singh, A. P.; Pandey, B. Tetrahedron Lett. 1992, 33, 825.
19. (b) Villemin, D.; Labiad, B.; Hammadi, M. J. Chem. Soc., Chem. Commun. 1992, 1192.
20. (c) Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039.
21. (d) Olah, G. A.; Narang, S. C.; Meidar, D.; Salem, G. F. Synthesis 1981, 282.
22. (e) Maiti, A. K.; Basu, K.; Bhattacharyya, P. J. Chem. Res. (Synop) 1995, 108.
23. (f) Patney, H. K. Tetrahedron Lett. 1991, 32, 2259.
24. (g) Patney, H. K.; Margan, S. Tetrahedron Lett. 1996, 37, 4621.
25. (h) Kamitori, Y.; Hojo, M.; Masuda, R.; Kimura, T.; Yoshida, T. J. Org. Chem. 1986, 51, 1427.
26. (a) Park, J. H.; Kim, S. Chem. Lett. 1989, 629.
27. (b) Tani, H.; Masumoto, K.; Inamasu, T. Suzuki, H. Tetrahedron Lett. 1991, 32, 2039.
28. (c) Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665.
29. (d) Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1998, 739.
30. (e) Jnaneshwara, G. K.; Barhate, N. B.; Sudalai, A.; Deshpande, V. H.; Wakharkar, R. D.; Gajare, A. S.; Shingare, M. S.; Sukumar, R. J. Chem. Soc., Perkin Trans. 1 1998, 965.
31. (f) Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 319.
32. (a) Cornellis, A.; Laszlo, P. Synlett 1994, 155.
33. (b) McKillop, A.; Young, D. W. Synthesis 1979, 401 and 481.
34. (c) Laszlo, P. Preparative Chemistry Using Supported Reagents, Academic Press: San Diego 1987.
35. (d) Laszlo, P.; Cornellis, A. Aldrichimica Acta. 1988, 21, 97.
36. We have repeated thioacetalization of benzaldehyde with Hojo's silica chloride and ours. The reactions were completed in 5 and 0.5h respectively, which shows that our catalyst is ten times more reactive than Hojo's catalyst.
37. Saunders, D. H.; Barford, R. A.; Magidman, P.; Olszewski, L. T., Rothbart, H. L. Anal.Chem. 1974, 46, 83