Skip to main content
SpringerLink
Log in

Mechanism of ruthenium tetroxide-catalysed oxidation of aldoses by alkalineN-bromoacetamide

  • Full Papers
  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Summary

The kinetics of oxidation of three aldoses (glucose, mannose and galactose) byN-bromoacetamide (NBA) in the presence of an alkaline solution of RuO4 as catalyst and Hg(OAc)2 as co-catalyst and as a scavenger for bromide have been investigated. The main products of the oxidation are the corresponding aldonic acids. The reaction is zero order with respect to aldose and OH−. First order dependence of the reaction on both NBA and RuO4 at low concentrations shifts to zero order at higher concentrations. Addition of acetamide decreases the reaction rate, while addition of Hg(OAc)2 has the opposite effect. No significant effect of ionic strength was observed. OBr− is postulated as the reactive oxidising species and a mechanism involving co-catalysis by RuO4 and HgII is proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. E. A. Shilov and A. A. Yamsikov.Ukrain. Khim. Zhur.,5, 595 (1967).

    Google Scholar 

  2. N. Bhattacharya and M. L. Sen Gupta,Indian J. Chem.,5, 554 (1967).

    CAS  Google Scholar 

  3. O. G. Ingles and G. C. Israel,J. Chem. Soc., 810 (1948).

  4. H. S. Isbell,J. Res. Bur. Stand.,8, 615 (1932);18, 505 (1937);18, 141 (1937);J. Am. Chem. Soc.,54, 1692 (1932);55, 2166 (1933).

    CAS  Google Scholar 

  5. I. R. L. Barker, W. G. Overend and C. W. Rees,Chem. & Ind., 1297 (1960).

  6. B. Singh, A. K. Singh, V. K. Singh, A. K. Sisodia and M. B. Singh,J. Mol. Catal.,40, 49 (1987).

    Article  CAS  Google Scholar 

  7. J. P. Sharma, R. N. P. Singh, A. K. Singh and B. Singh,Tetrahedron,42, 2739 (1986).

    Article  CAS  Google Scholar 

  8. B. Singh, A. K. Singh and D. Singh,J. Mol. Catal.,48, 207 (1988).

    Article  CAS  Google Scholar 

  9. B. Singh, D. Singh and A. K. Singh,Intl. J. Chem. Kinetics,20, 501 (1988).

    Article  CAS  Google Scholar 

  10. N. Venkatasubramaniam and V. Thiagarajan,Can. J. Chem.,47, 694 (1969).

    Article  Google Scholar 

  11. M. K. Reddy, CH. S. Reddy and E. V. Sundaram,Tetrahedron,41, 3071 (1985).

    Article  CAS  Google Scholar 

  12. T. D. Avtokratova,Analytical Chemistry of the Elements, Ann Arbor-Humphrey Science Pub., 1969, p. 146.

  13. I. L. Finar,Organic Chemistry, Vol. 1, Longman, 6th Edition, 1973, p. 574.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Allahabad, 211 002, Allahabad, India

    Ashok K. Singh, Amar Singh, Ranjana Gupta, Madhu Saxena & Bharat Singh

Authors
  1. Ashok K. Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amar Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ranjana Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Madhu Saxena
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bharat Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

TMC 2588

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singh, A.K., Singh, A., Gupta, R. et al. Mechanism of ruthenium tetroxide-catalysed oxidation of aldoses by alkalineN-bromoacetamide. Transition Met. Chem. 17, 413–416 (1992). https://doi.org/10.1007/BF02910720

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02910720

Keywords

Search

Navigation