Summary
The kinetics and mechanism of oxidation of a series of alcohols, namely cyclohexanol, cyclopentanol, pentan-2-ol and benzyl alcohol, by silver(II) perchlorate in perchloric acid solution. have been investigated by the stopped-flow technique. These oxidations proceed through two parallel pathways involving Ag2+ and AgOH+ species. In the case of benzyl alcohol, the hydroxo species, which has been found to be almost universally reactive toward different organic substrates, is inactive; this behaviour has been interpreted in terms of interaction of the oxidant with the aromatic moiety in the alcohol. The reactivities are discussed in terms of substrate reaction sites with reference to electronic availability and reaction products.
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References
Part 4: C. Baiocchi and E. Mentasti,Internat. J. Chem. Kin., in press.
C. Walling and D. M. Camaioni,J. Org. Chem., 43, 3266 (1978).
E. Mentasti, E. Pelizzetti and C. Baiocchi,J. Chem. Soc. Perkin Trans. 11, 77 (1978).
E. Pelizzetti and E. Mentasti,J. Chem. Soc. Dalton Trans., 2086 (1975).
D. S. Honig and K. Kustin,J. Inorg. Nucl. Chem., 32, 1599 (1970).
G. Giraudi. E. Mentasti and E. Pelizzetti,Accad. Sci. Atti Torino, 108, 825 (1974).
E. Pelizzetti, E. Mentasti and C. Baiocchi,J. Inorg. Nucl. Chem., 38, 557 (1976).
P. O'Neill. S. Steenken and D. Schulte-Frohlinde,J. Phys. Chem., 79. 2773 (1975).
H. B. Mark Jr. and G. A. Rechnitz.Kinetics in Analytical Chemistry, Interscience, New York 1968, ch 6.
J. Hine.Physical Organic Chemistry, McGraw-Hill, New York 1962, ch 4.
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Baiocchi, C., Mentasti, E. Kinetics of oxidation of organic compounds by silver(II) in aqueous perchloric acid solution. Part 5. Transition Met Chem 5, 259–262 (1980). https://doi.org/10.1007/BF01396932
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DOI: https://doi.org/10.1007/BF01396932