Polyaniline supported cobalt(II) catalyst: Oxidation of alkenes with molecular oxygen

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1235-1238

  Das, Bhaskar C ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE;

ARTICLE; CATALYST; DRUG SYNTHESIS; EPOXIDATION; METHODOLOGY; REACTION ANALYSIS;

EID: 0031575648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00045-2     Document Type: Article

References (15)

1. 1 a) Sheldon, R. A.; Kochi, J. K., Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1991.
2. b) Mimoun, H. Comprehensive Coordination Chemistry; Pergamon press: Oxford, 6, 1987
3. c) Hamilton, D. E.; Drago, R. S.; Zombeck, A. J.Am.Chem.Soc. 1987, 109, 374.
4. d) Yamada, T.; Takai, T.; Rhode, O.;, Mukaiyama, T.; Chem. Lett. 1991, 1.
5. e) Barton, D. H. R.; Beviere, S. D.; Chavasiri, W.; Csuhai, E.; Doller, D.; Tetrahedron, 1992, 48, 2895.
6. f) Tateiwa, T.; Horiuchi, H.; Umura, S. J. Chem. Soc. Chem. Commun. 1994, 2567.
7. 2. Hirao, T.; Higuchi, M.; Hanata, B.; Ikeda, I. Tetrahedron Lett. 1995, 36, 5925.
8. 3. a) Polyaniline in the form of polyleucoemeraldine was prepared according to the reference 3b and used without purification or molecular weight determination. To the best of our knowledge no other analogue of polyaniline supported cobalt complex is known in the literature.
9. b) Hasik, M.; Turek, W.; Stochmal, E.; Lapkowski, M.; Pron, A J. Catal. 1994, 147, 544.
10. 4. Preparation of polyaniline supported cobalt(II) catalyst: A mixture of polyaniline (200 mg) and cobalt acetate (200 mg, 1:1=w/w) was stirred in acetonitrile and acetic acid (1:1=V/V) for 72 h at room temperature The reaction mixture was filtered and the solid catalyst washed with acetonitrile until the filtrate became colourless. The catalyst was dried at 110 - 120° C.
11. 5 General procedure : A mixture of alkene (5 mmol), 2-methylpropanal (15 mmol) and catalyst (5 mol%) were dissolved in acetonitrile (30 mL) in an oxygen atmosphere at room temperature. After completion of the reaction (monitored by TLC), the catalyst was filtered and the solvent was evaporated and the residue purifed by column chromatography.
12. 6. Banfi, S.; Colonna, S.; Molinari, H. and Julia, S.; Guixer, J. Tetrahedron, 1984, 40, 5207.
13. 7. Punniyamurthy, T.; Reddy, M. M.; Kalra, S. J. S.; Iqbal, J. Pure & Appl. Chem. 1996, 68, 619.
14. 8 Mandal, A. K.; Iqbal, J.; J.Org. Chem. 1996 (submitted).
15. 9. Jones, R. D. ; Summerville, D. A.; Basolo, F. Chem. Rev. 1979, 79, 139.