Palladium(II)-catalyzed oxidation of primary amines by bromamine-T in alkaline medium: A kinetic and mechanistic study

Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry

Volumn 33, Issue 7, 2003, Pages 1145-1156

  Kondarasaiah, M H ^a   Ananda, S ^a   Puttaswamy, ^b   Made Gowda, N M ^c  

^a UNIVERSITY OF MYSORE   (India)

^b BANGALORE UNIVERSITY   (India)

^c WESTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI; AMINE; BROMAMINE T; CHLORIDE ION; HEXYLAMINE; PALLADIUM; PROPANE; SODIUM HYDROXIDE; SOLVENT; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; DIELECTRIC CONSTANT; KINETICS; OXIDATION; PARAMETER; REACTION ANALYSIS; REDUCTION; TEMPERATURE;

EID: 0042423594     PISSN: 00945714     EISSN: None     Source Type: Journal    
DOI: 10.1081/SIM-120023483     Document Type: Article

References (20)

1. Campbell, M.M.; Johnson, G. Chloramine-T and related N-halogeno-N-metallo reagents. Chem. Rev. 1978, 78, 65-79.
2. Banerji, K.K.; Jayaram, B.; Mabadevappa, D.S. Mechanistic aspects of oxidations by N-metallo-N-halorylsulfonamides. J. Sci. Ind. Res. 1987, 46, 65-76.
3. Ruff, F.; Kucsman, A. Mechanism of the reaction of dialkyl sulphides with bromamine-T. J. Chem. Soc., Perkin Trans. II 1982, 1075-1079.
4. Mahadevappa, D.S.; Puttaswamy. Kinetics of oxidation of aliphatic ketones with bromamine-T in acid medium. Bull. Chem. Soc. Jpn. 1988, 61, 543-547.
5. Rangappa, K.S.; Ramachandra, H.; Mahadevappa, D.S.; Made Gowda, N.M. Osmium(VIII) catalyzed kinetics and mechanism of indoles oxidation with aryl-N-haloamines in alkaline medium. Int. J. Chem. Kinet. 1996, 28, 265-274.
6. Shukla, A.; Upadhyay, S.K. Kinetics and mechanisms of Pd(II) catalyzed oxidation of some primary amines and amino alcohols by alkaline hexacyanoferrate(III). Indian J. Chem. 1995, 34A, 120-123.
7. Ananda, S.; Demappa, T.; Mahadevappa, D.S.; Made Gowda, N.M. Oxidation of some primary amines by bromamine-B in alkaline medium: a kinetic and mechanistic study. Int. J. Chem. Kinet. 1996, 28, 873-878.
8. Ananda, S.; Demappa, T.; Made Gowda, N.M. Oxidation of primary amines by bromamine-B catalyzed by osmium(VIII) in alkaline medium: a kinetic and mechanistic study. Int. J. Chem. Kinet. 1997, 29, 737-744.
9. Ahmed, M.S.; Mahadevappa, D.S. Bromamine-B as a new oxidimetric titrant. Talanta 1980, 27, 669-670.
10. Nair, C.G.R.; Indresenan, P. New redox titrants in non-aqueous or partially aqueous media VI*. Potentiometric determinations using dibromamine-T and some further applications of dichloramine-T. Talanta 1976, 23, 239-241.
11. Feigl, F. Spot Tests in Organic Analysis; Elsevier: Amsterdam, 1975; 247.
12. Rangappa, K.S.; Manjunathaswamy, H.; Raghavendra, M.P.; Made Gowda, N.M. Kinetics and mechanism of oxidation of neutral α-amino acids by sodium-N-chloro-p-toluenesulfonamide in acid medium. Int. J. Chem. Kinet. 2002, 34, 49-55.
13. Soper, F.G. Hydrolysis of the p-toluenesulfochloroamides in water. J. Chem. Soc. Trans. 1924, 125, 1899-1910.
14. Morris, J.C.; Salazar, J.A.; Wineman, M.A. Equilibrium studies on chloro compounds: the ionization constant of N-chloro-p-toluenesulfonamide. J. Am. Chem. Soc. 1948, 70, 2036-2041.
15. Bishop, E.; Jennings, V.J. Titrimetric analysis with chloramine-T. I. The status of cbloramine-T as a titrimetric reagent. Talanta 1958, 1, 197-199.
16. Hardy, F.E.; Johnston, J.P. The interaction of N-bromo-N-sodiobenzene-sulphonamide (bromamine-B) with p-nitrophenoxide ion. J. Chem. Soc., Perkin Trans. II 1973, 742-746.
17. 2- in aqueous solution. Organometallics 1988, 7, 1677-1681.
18. Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th Ed.; John Wiley and Sons, Inc.: New York, 1988.
19. Sukla, A.; Upadyaya, S.K. Kinetics and mechanism of Pd(II) catalyzed oxidation of mandelic and tartaric acids by chloramine-T in aklaline medium. Indian J. Chem. 1991, 30A, 154-157.
20. Molelwyn, E.A.; Hughes, J. Kinetics of Reactions in Solutions; Oxford University Press: London, 1947; 297-299.