AlCl3·6H2O/KI/CH3CN/H 2O: An efficient and versatile system for chemoselective C-O bond cleavage and formation of halides and carbonyl compounds from alcohols in hydrated media

Synthetic Communications

Volumn 36, Issue 9, 2006, Pages 1259-1264

  Gogoi, Pranjal ^a   Konwar, Dilip ^a   Sharma, Saikat Das ^a   Gogoi, Prodip Kumar ^b  

^a REGIONAL RESEARCH LABORATORY   (India)

^b DIBRUGARH UNIVERSITY   (India)

Author keywords

AlCl3 6H2O KI CH3CN; Chemoselective; Cleavage of C O bonds; Halide formation and oxidation; Hydrated media; System

Indexed keywords

ACETAL; ALCOHOL; ALUMINUM CHLORIDE; CARBON; CARBONYL DERIVATIVE; ESTER; HALIDE; OXYGEN;

ARTICLE; CHEMICAL BOND; HYDRATION; OXIDATION KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33645363274     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500516316     Document Type: Article

References (23)

1. (a) Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981;
2. (b) Gogoi, P.; Hazarika, P.; Konwar, D. J. Org. Chem. 2005, 70, 1934.
3. Sartori, G.; Bollini, R.; Bigi, F.; Boica, G.; Maggi, R.; Right, P. Chem. Rev. 2004, 104, 199.
4. Feixas, J.; Capdevila, A.; Camps, F.; Guerrero, A. J. Chem. Soc., Chem. Commun. 1992, 1451.
5. Deville, J. P.; Behar, V. J. Org. Chem. 2001, 66, 4097.
6. Habibi, M. H.; Tangestaninejad, S.; Mohammadpoor Baltork, I.; Mirkhani, V.; Yadollahi, B. Tetrahedron Lett. 2001, 42, 6771.
7. Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
8. Cotelle, P.; Catteau, J.-P. Tetrahedron Lett. 1992, 33, 3855.
9. Gaunt, M. J.; Yu, J.; Spencer, J. B. J. Org. Chem. 1998, 63, 4172.
10. Chavan, S. P.; Zubaidha, P. K.; Dantale, S. W.; Keshavaraja, A.; Ramaswamy, A. V.; Ravindranathan, T. Tetrahedron Lett. 1996, 37, 237.
11. Park, K. H.; Yoon, Y. J.; Lee, S. G. Tetrahedron Lett. 1994, 35, 9737.
12. Landini, D.; Rolla, F. J. Org. Chem. 1982, 47, 154.
13. Jung, M. E.; Andrus, W. A.; Ornstein, P. L. Tetrahedron Lett. 1977, 4175.
14. Mandal, A. K.; Shrotri, P. Y.; Ghogare, A. D. Synthesis 1986, 221.
15. Balme, G.; Gore, J. J. Org. Chem. 1983, 48, 3336.
16. Sterzycki, R. Synthesis 1979, 724.
17. Corey, E. J.; Tius, M. A. Tetrahedron Lett. 1977, 24, 2081.
18. Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 612.
19. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
20. Whitesides, G. M.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1985, 24, 617.
21. Boruah, M.; Konwar, D. J. Org. Chem. 2002, 67, 7138-7139.
22. Boruah, M.; Konwar, D. Synlett 2001, 795.
23. Green Wood, N. N.; Eanndshow, A. Chemistry of Elements; Pergamon Press: New York, 1984; p. 254.