Investigations towards the chemoselective thioacetaliztion of carbonyl compounds by using ionic liquid [bmim]Br as a recyclable catalytic medium

Advanced Synthesis and Catalysis

Volumn 346, Issue 5, 2004, Pages 579-582

  Kamal, Ahmed ^a   Chouhan, Gagan ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1 n butyl 3 methylimidazolium bromide; Aldehydes; Chemoselectivity; Ionic liquid; Thioacetalization; Thioacetals

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM; BROMINE; CARBONYL DERIVATIVE; CATION; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; CATALYSIS; CATALYST; HAZARD; LIQUID CULTURE; REVIEW; WASTE;

EID: 2542450803     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303171     Document Type: Review

References (30)

1. a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd edn., Wiley, New York, 1999, p. 293;
2. b) P. J . Kocieński, Protecting Groups, 3rd edn., Thieme, Stuttgart, 2004, p. 77.
3. a) S. Muthusamy, S. Arulananda Babu, C. Gunanathan, Tetrahedron Lett. 2001, 42, 359;
4. b) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, J. Org. Chem. 2001, 66, 7527, and references cited therein;
5. c) H. Tani, K. Masumoto, T. Inamasu, Tetrahedron Lett. 1991, 32, 2047.
6. A. T. Khan, E. Mondal, P. R. Sahu, S. Islam, Tetrahedron Lett. 2003, 44, 919.
7. S. K. Day, Tetrahedron Lett. 2004, 45, 1035.
8. H. Firouzabadi, S. Eslami, B. Karimi, Bull. Chem. Soc. Jpn. 2001, 74, 2401.
9. a) A. Kamal, G. Chouhan, Tetrahedron Lett. 2002, 43, 1347;
10. b) A. Kamal, G. Chouhan, Synlett 2002, 474;
11. c) A. Kamal, G. Chouhan, Tetrahedron Lett. 2003, 44, 3337.
12. a) G. Centi, S. Perathoner, Catal. Today 2003, 77, 287;
13. b) P. T. Anastas, J. C. Warner, Green Chemistry; Theory and Practice, Oxford University Press, New York, NY, 1998;
14. c) P. Tundo, P. T. Anastas, Green Chemistry; Theory and Practice, Oxford University Press, New York, NY, 1999.
15. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
16. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
17. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
18. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
19. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
20. For excellent reviews, see a) J. D. Holbrey, K. R. Seddon, Clean. Prod. Process. 1999, 1, 223; b) T. Welton, Chem. Rev. 1999, 99, 2071; c) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772; d) R. Sheldon, Chem. Commun. 2001, 2399; e) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A. 2002, 182-183, 419; f) J. Dupont, R. F. Desouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.
21. T. Fischer, A. Sethi, T. Welton, J. Woolf, Tetrahedron Lett. 1999, 40, 793.
22. H. P. Zhu, F. Yang, J. Tang, M. Y. He, Green Chem. 2003, 5, 38.
23. D. V. Jarikote, S. A. Siddiqui, R. Rajagopal, D. Thomas, R. J. Lahoti, K. V. Srinivasan, Tetrahedron Lett. 2003, 44, 1835.
24. a) S. Park, R. J. Kazalauskas, J. Org. Chem. 2001, 66, 839 5;
25. b) P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. De. Souza, J. Dupont, Polyhedron, 1996, 15, 1217.
26. X. Lijin, W. Chen, J. Xiao, Organometallics 2000, 19, 1123.
27. 3 in small amounts with vigorous stirring until no bubbling was observed from the ionic liquid water mixture, then methanol was added to this mixture and water was removed azeotropically at 80°C under high vacuum, later dichloromethane was added, the mixture filtered and the filtrate dried on sodium sulfate, finally concentration under vacuum at 80°C provided the neutral ionic liquid.
28. C. Thomazean, H. Olivier-Bourbigou, L. Magna, S. Luts, B. Gilbert J. Am. Chem. Soc. 2003, 125, 5264.
29. J. S. Yadav, B. V. S. Reddy, S. K. Panday, Synlett 2001, 238.
30. V. G. Saraswathy, S. Sankararaman, J. Org. Chem. 1994, 59, 4665.