Copper (II) Mediated Oxidative Alkoxylation of White Phosphorus. Communication 1.

Authors

  • R. R. Abdreimova D.V. Sokolsky Institute of Organic Catalysis and Electrochemistry, 142 Kunaev St., 050010 Almaty, Kazakhstan
  • F. Kh. Faizova D. V. Sokolsky Institute of Organic Catalysis and Electrochemistry, 142 Kunaev St., 050010 Almaty, Kazakhstan
  • A. A. Karimova D. V. Sokolsky Institute of Organic Catalysis and Electrochemistry, 142 Kunaev St., 050010 Almaty, Kazakhstan

DOI:

https://doi.org/10.18321/ectj53

Abstract

White phosphorus has been oxidized by copper (II) acetylacetonate, halides or carboxylates in aliphatic alcohols to yield dialkyl phosphates and trialkyl phosphates under inert atmosphere and mild reaction conditions. Trialkyl phosphite has been observed as unstable organophosphorus intermediate, which is being converted into the main reaction products. In the case of methanolic solutions, the derivatives of two step acidolysis of dimethyl phosphite, monomethyl phosphite and phosphorous acid, have been additionally detected among the reaction products. The influence of the copper (II) oxidants on the kinetics of accumulation and transmutation of organophosphorus products has been explored. The order of oxidative ability of the copper (II) compounds has been established. The major steps of the reaction including (i) the coordination of white phosphorus and alcohol to metal ion and (ii) the redox decomposition of this intermediate complex accompanied by reducing elimination of elementary copper and formation of organophosphorus product have been also suggested.

References

1. Van Wazer, J. R. Phosphorus and its compounds. Wiley, New York, 1958, p. 91.

2. Nikandrov, I. S., Semkin, N. T., and Kogtev, S. E., The items of kinetics and catalysis, Ivanovo, 1980, p. 87.

3. Dorfman, Ya. A., Abdreimova, R. R., and Doroshkevich, D. M., Teoret. Experim. Khim.27:659 (1991).

4. Dorfman, Ya. A., Abdreimova, R. R., and Doroshkevich, D. M., Koord. Khim. 20:304 (1994).

5. Perrin, D. D., and Armarengo, W. L. F., Purification of Laboratory Chemicals; Pergamon Press: Oxford (1980).

6. Postnikov, N. N., The thermal phosphoric acid. The chemistry and technology, Moscow, Khimiya, 1970, p. 131.

7. Okamoto, Y., Kusano, T., and Takamuku, S., Bull. Chem. Soc. Jpn. 61:3359 (1988).

8. Budnikova, Yu. H., Kafiyatullina, A. G., Sinyashin, O. G., and Abdreimova R. R., Russian Chemical Bulletin. International edition 4:929 (2003).

9. Dorfman, Ya. A., Abdreimova, R. R., and Akbayeva, D. N., Kin. Kat. 36:103 (1995).

10. Kaslina, N. A., Kriniztkaya, L. V., Kessenikh, A. V., Balashova, T. V., and Reshetnikov, Yu. P., Zh. Obsh. Chim. 62:1531 (1992).

11. Fakhraian, H., and Mirzaei, A., Org. Proc. Res. Develop. 8:401 (2004).

12. Brown, C., Hudson, R. F., and Wartew, G. A., J. Chem. Soc., Chem. Comm., 3:7 (1978).

13. Riesel, L., Kant, M., and Helbing, R. Z., Anorg. Allg. Chem., 580:217 (1990).

14. Lutsenko, I. F., and Proskurnina, M. V., Usp. Khim. 47:1648 (1978).

15. Corbridge, D. E. C. Phosphorus an Outline of its Chemistry, Biochemistry and Technology, 5th Ed., Elsevier, Amsterdam, 1995, p. 23.

16. Arbuzov A. E. Izbrannye trudy po khimii fosfororganocheskikh soedineniy (Selected works on the chemistry of organophosphorus compounds). Moscow: Nauka, 1977, p. 123.

17. Morrison, R. T.; Boyd, R. N. Organic Chemistry. Second edition. Allyn and Bacon, Inc., Boston, 1970, p. 23.

18. Huheey, J. E. Inorganic chemistry. Principles of structure and reactivity, Haper & Row, New York, 1985, p. 512.

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Published

2010-11-15

How to Cite

Abdreimova, R. R., Faizova, F. K., & Karimova, A. A. (2010). Copper (II) Mediated Oxidative Alkoxylation of White Phosphorus. Communication 1. Eurasian Chemico-Technological Journal, 12(3-4), 259–265. https://doi.org/10.18321/ectj53

Issue

Vol. 12 No. 3-4 (2010)

Section

Articles

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