Tungsten hexachloride (WCl6) as an efficient catalyst for chemoselective dithioacetalization of carbonyl compounds and transthioacetalization of acetals

Synlett

Volumn , Issue 7, 1998, Pages 739-740

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Karimi, Babak ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001434522     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1756     Document Type: Article

References (29)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991.
2. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075, 1077.
3. Seebach, D. Angew. Chem., Int. Ed. Engl. 1969, 8, 639.
4. Grobel, B. T.; Seebach, D. Synthesis 1977, 357.
5. Bulman Page, P. C.; VanNiel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643.
6. Pettit, G. R.; Van Tamelen, E. E. Org. React. 1962, 12, 356.
7. Fieser, L. F. J. Am. Chem. Soc. 1954, 76, 1945.
8. Evans, D. A.; Truesdale, L. K.; Grimm, K. G.; Nesbitt, S. L. J. Am. Chem. Soc. 1977, 99, 5009.
9. Truce, W. E.; Roberts, F. E. J. Org. Chem. 1963, 28, 961.
10. Galaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31, 581.
11. Hauptmann, H.; Moura Campos, M. J. Am. Chem. Soc. 1950, 72, 1405.
12. Seebach, D.; Kolb, M. Chem. Ind. (London) 1974, 687.
13. Ong, B. S. Tetrahedron Lett. 1980, 4225.
14. Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24, 1289.
15. Tani, H.; Masumoto, K.; Ihamasu, T. Tetrahedron Lett. 1991, 32, 2039.
16. Ku, B.; Oh, D. Y. Synth. Commun. 1989, 19, 433.
17. Ong, B. S.; Chan, T. H. Synth. Commun. 1977, 7, 283.
18. Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169.
19. Chowdhury, P. K. J. Chem. Res.(Synop), 1993, 124.
20. Das, N. B.; Nayak, A.; Sharma, R. P. J. Chem. Res.(Synop), 1993, 242.
21. Komatsu, N.; Uda, M.; Suzuki, H. Synlett 1995, 984.
22. Geetha, V.; Sankararaman, S. J. Org. Chem. 1994, 52, 4665.
23. Patney, H. K. Tetrahedron Lett. 1991, 32, 2259.
24. Patney, H. K.; Margan, S. Tetrahedron Lett. 1996, 37, 4621.
25. Kamitori, Y.; Hojo, M.; Masuda, R.; Kimura, T.; Yoshida, T. J. Org. Chem. 1986, 51, 1427.
26. Olah, G. A.; Narang, S. C.; Meidar, D.; Salem, G. F. Synthesis 1981, 282.
27. Maiti, A. K.; Basu, K.; Bhattacharyya, P. J. Chem. Res.(Synop), 1995, 108.
28. Firouzabadi, H. Shiriny, F. Tetrahedron 1996, 52, 14929.
29. 4. Evaporation of the solvent under reduced pressure gave the almost pure dithioacetal. Further purification was performed by column chromatography on silica gel using petroleum ether as eluent followed by bulb to bulb distillation or recrystallization to afford the desired product in good to excellent yield (Table 1).