Effect of cyclodextrin complexation in bromine addition to unsymmetrical olefins: Evidence for participation of cyclodextrin hydroxyl groups

Organic and Biomolecular Chemistry

Volumn 3, Issue 6, 2005, Pages 1008-1012

  Manickam, Manickam C Durai ^a   Annalakshmi, Subramanian ^a   Pitchumani, Kasi ^a   Srinivasan, Chockalingam ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ADDITION REACTIONS; BROMINE; CHEMICAL BONDS; COMPLEXATION; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; STEREOCHEMISTRY;

BROMINATION; CYLODEXTRINS; DIBROMIDES (DB); STEREOSELECTIVITY;

OLEFINS;

EID: 16244411951     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418685k     Document Type: Article

References (36)

1. (a) I. Tabushi, K. Yamamura, K. Fujita and H. Kawakubo, J. Am. Chem. Soc., 1979, 101, 1019;
2. (b) Y. Ihara, E. Nakanishi, M. Nango and J. Koga, Bull Chem. Soc. Jpn., 1986, 59, 1901.
3. (a) K. Pitchumani, M. C. Durai Manickam and C. Srinivasan, Tetrahedron Lett., 1991, 32, 2975;
4. (b) K. Pitchumani, M. C. Durai Manickam and C. Srinivasan, J. Photochem. Photobiol, A, 2002, 149, 131.
5. (a) K. Pitchumani, P. Velusamy and C. Srinivasan, Tetrahedron, 1994, 50, 12979;
6. (b) A. Ueno, Supramol. Sci., 1996, 3, 31.
7. (a) M. S. Syamala and V. Ramamurthy, Tetrahedron, 1988, 44, 7234;
8. (b) G. Dasaratha Reddy, G. Usha, K. V. Ramanathan and V. Ramamurthy, J. Org. Chem., 1986, 51, 3085.
9. N. Baba, Y. Matsumura and T. Sugimoto, Tetrahedron Lett., 1978, 19, 4281.
10. S. Banfi, S. Colonna and S. Julia, Synth. Commun., 1983, 13, 1049.
11. A. W. Czarnik, J. Org. Chem., 1984, 49, 924.
12. J. Drabowicz and M. Mikolajczyk, Phosphorus Sulfur Relat. Elem., 1984, 21, 245.
13. Y. Tanaka, H. Sakuraba and H. Nakanishi, J. Chem. Soc., Chem. Commun., 1983, 947.
14. M. F. Ruasse, Acc. Chem. Res., 1990, 23, 87.
15. G. Bellucci, R. Bianchini, C. Chiappe, R. S. Brown and H. S. Tilk, J. Am. Chem. Soc., 1991, 113, 8012.
16. G. Bellucci, C. Chiappe, R. Bianchini, D. Lenoir and R. Herges, J. Am. Chem. Soc., 1995, 117, 12001.
17. G. Bellucci, R. Bianchini and C. Chiappe, J. Org. Chem., 1991, 56, 3067.
18. M. F. Ruasse, G. L. Moro, B. Galland, R. Bianchini, C. Chiappe and G. Bellucci, J. Am. Chem. Soc., 1997, 119, 12492.
19. M. C. Durai Manickam, K. Pitchumani and C. Srinivasan, J. Inclusion Phenom. Macrocyclic Chem., 2002, 43, 207.
20. R. E. Buckles, J. M. Bader and R. J. Thurmaier, J. Org. Chem., 1962, 27, 4523.
21. J. H. Rolston and K. Yates, J. Am. Chem. Soc., 1969, 91, 1469.
22. S. D. Young and E. Berliner, J. Org. Chem., 1979, 44, 1088.
23. J. A. Pincock and K. Yates, Can. J. Chem., 1970, 48, 3332.
24. H. Sakuraba, H. Ishizaki, Y. Tanaka and T. Shimizu, J. Inclusion Phenom., 1987, 5, 449.
25. O. S. Tee and J. M. Bennett, J. Am. Chem. Soc., 1988, 110, 3226.
26. (a) J. I. Choe and S. K. Chang, Bull. Korean Chem. Soc., 2002, 23;
27. (b) Discover User Guide, Accelrys Inc., 2001.
28. (a) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr., 1990, 13, 470;
29. (b) Z. Chen, J. S. Bradshaw and M. L. Lee, Tetrahedron Lett., 1996, 37, 6831;
30. (c) J. L. Mieusset, D. Krois, M. Pacar, L. Brecker, G. Giester and U. H. Brinker, Org. Lett., 2004, 6, 1967.
31. (a) K. Pitchumani, S. Devanathan and V. Ramamurthy, J. Photochem. Photobiol, A: Chem., 1992, 69, 201;
32. (b) G. Dasaratha Reddy and V. Ramamurthy, J. Org. Chem., 1987, 52, 3952.
33. H. A. Benesi and J. H. Hildebrand, J. Am. Chem. Soc., 1949, 71, 2703.
34. P. V. Demarco and A. V. Thakkar, J. Chem. Soc., Chem. Commun., 1970, 2.
35. S. Kalo, Bull. Inst. Phys. Chem. Res., 1932, 11, 756, (CA, 1932, 26, 5260).
36. S. Kalo, Bull. Inst. Phys. Chem. Res., 1932, 11, 756, (CA, 1932, 26, 5260).