Methyltrioxorhenium Catalyzed Oxidative Cleavage of α -Hydroxycarbonyl Compounds to Carboxylic Acids with Hydrogen Peroxide

Synthetic Communications

Volumn 33, Issue 22, 2003, Pages 3875-3878

  Jain, Suman L ^a   Sharma, Vishal B ^a   Sain, Bir ^a  

^a CSIR INDIAN INSTITUTE OF PETROLEUM   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CARBOXYLIC ACID; HYDROGEN PEROXIDE; HYDROXYL GROUP; METHYLTRIOXORHENIUM; RHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; SYNTHESIS;

EID: 0345276569     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026309     Document Type: Article

References (21)

1. Shing, T.K.M. Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: New York, 1991; Vol. 7, 703 p.
2. (a) Clutterbuck, P.W.; Renter, F. J. Chem. Soc. 1935, 1467;
3. (b) Shiner V.J., Jr.; Wasmuth, C.S. J. Am. Chem. Soc. 1959, 81, 37.
4. Baer, E. J. Am. Chem. Soc. 1940, 62, 1597.
5. Nwauka, S.O.; Keehn, P.M. Tetrahedron Lett. 1982, 23, 3135.
6. Ali, B.E.; El-Ghanam, A.M.; Fettouhi, M. J. Mol. Catal. A: Chem. 2001, 165, 283.
7. Shimizu, M.; Orita, H.; Suzuki, K.; Hayakawa, T.; Hamakawa, S.; Takehira, K. J. Mol. Catal. A: Chem. 1996, 114, 217.
8. Herrmann, W.A.; Kuhn, F.E. Acc. Chem. Res. 1997, 30, 169.
9. For reviews see: (a) Romao, C.C.; Kuhn, F.E.; Herrmann, W.A. Chem. Rev. 1997, 97, 3197;
10. (b) Espenson, H. Chem. Commoun. 1999, 479;
11. (c) Owens, S.; Arias, J.; Abu-Omar, M.M. Catal. Today 2000, 55, 317;
12. (d) Herrmann, W.A.; Kuhn, F.E. Acc. Chem. Res. 1997, 30, 169.
13. (a) Jain, S. L.; Sain, B. Chem. Commun. 2002, 1040;
14. (b) Sharma, V.B.; Jain, S.L.; Sain, B. Tetrahedron Lett. 2003, 44, 383;
15. (c) Jain, S.L.; Sain, B. J. Mol. Catal. 2001, 176, 102;
16. (d) Rao, T.V.; Sain, B.; Kumar, K.; Murthy, P.S.N.; Prasada Rao, T.S.R.; Joshi, G.C. Synth. Commun. 1998, 28, 319;
17. (e) Sain, B.; Murthy, P.S.N.; Rao, T.V.; Prasada Rao, T.S.R.; Joshi, G.C. Tetrahedron Lett. 1994, 35, 5083.
18. (a) Adams, R.; Marvell, C.S. Org. Synth. Coll. 1941, 1, 94;
19. (b) McElvain, S.M. Org. Reactions 1948, 4, 256.
20. Kirihara, M.; Takizawa, S.; Momose, T. J. Chem. Soc. Perkin Trans. I 1998, 7.
21. 2 (for destruction of H202) followed by filtration and passing through a short column of silica gel using dichloromethane as eluent, evaporation of the solvent gave benzoic acid (234mg, 96%). Other α-hydroxycarbonyl compounds were oxidized using this procedure and their reaction times and yields are given in Table 1. The products were identified by comparing their physical and spectral data with those of authentic samples reported in literature. In case of asymmetric α-hydroxycarbonyl compounds the identity of the acids was established through GC by comparing the retention time of their methyl esters with those of authentic samples. Similarly α-dicarbonyl compounds (benzil and anisil) were oxidized to their corresponding acids.