medigraphic.com
ISSN 2395-8723 (Electronic)
ISSN 1405-888X (Print)
TIP Revista Especializada en Ciencias Químico-Biológicas

2011, Number 1

<< Back Next >>

TIP Rev Esp Cienc Quim Biol 2011; 14 (1)

Teoría de la regioquímica en la nitración con nitrato de acetilo y con ácido nítrico

Sánchez-Viesca F, Gómez MR, García JM

Language: Spanish
References: 23
Page: 24-29
PDF size: 176.29 Kb.


ABSTRACT

Although the structures of the reaction products obtained with different nitrating reagents are well known, a complete theory regarding the regiochemistry is missing. Even though the functional groups have been grouped according the exerted orientation in electrophilic substitution reactions, in many cases there is no explanation about the preponderance of one of the expected isomers. On the other hand, the preferent ortho orientation of acetyl nitrate in nitration reactions is well known. However, a causal explanation of this phenomenon has not been provided. In this communication a regiochemistry theory in acetanilide nitration is presented, both when sulfonitric mixture or when acetyl nitrate are used. This theory was confirmed by comparison to the experimental results obtained when these reactions were run with toluene or with anisole.


REFERENCES

  1. Fieser, L. F. & Fieser, M., Reagents for Organic Synthesis, p. 13 (J. Wiley, Nueva York, 1967).

  2. UK Chemical Reaction Hazards Forum, http://www.crhf.org.uk/ incident16.html

  3. Buckingham, J. & Donaghy, S. M., Dictionary of Organic Compounds, 5ª ed., vol. I (Chapman-Hall, Nueva York, 1982).

  4. National Institute of Standards and Technology (NIST), http:/ /webbook.nist.gov/cgi/cbook.cgi? ID=C591093&Units=SI&Mask=FFF

  5. Clauson-Kaas, N. & Fakstorp, J. The Structure of Marquis’ Nitroacetin. Acta Chem. Scand., 1, 210-215 (1947).

  6. Michels, J. G. & Hayes, K.J. Conversion of the Nitration Intermediate Derived from Furfural into 5-Nitro-2-furfural Diacetate. J. Am. Chem. Soc.,80, 1114-1116 (1958).

  7. Balina, G., Kesler, P., Petre, J., Pham, D. & Vollmar, A. Nitronium Acetate Adducts of Furan Derivatives. J. Org. Chem., 20, 3811-3818 (1986).

  8. Martínez-Crespo, C., Síntesis Industrial de Medicamentos, p. 258 (Dossat, Madrid, 1957).

  9. Vogel, A. I., Textbook of Practical Organic Chemistry, 5ª ed., pp. 919, 920 (Longman Scientific & Technical, Londres, 1989).

  10. Mann, F. G. & Saunders, B. C., Practical Organic Chemistry, 4ª ed., p. 165 (Longmans, Londres, 1962).

  11. Cumming, W. M., Hopper, I. V. & Wheeler, T. S., Systematic Organic Chemistry, 4ª ed., p. 280 (Constable, Londres, 1950).

  12. Giral, F. & Rojahn, C.A., Productos Químicos y Farmacéuticos, Vol. II, pág. 705 (Atlante, México D.F., 1956).

  13. Menke, J. B., Nitration of organic compounds. British Patent 235,698 (1924), Chem. Abstr., 20, 916-917 (1926).

  14. Menke, J. B., Nitrieren mit Nitraten, Rec. trav. chim., 44, 141- 149 (1925).

  15. Bahadur, K. & Patwardhan, W. D., Preparation of o-Nitroacetanilide. Curr. Sci., 37, 492 (1968).

  16. Cole-Palmer General Catalog, 2009/10, Nos. EW-88324-77 y - 78 (Cole-Palmer, Vernon Hills, Ill., 2009).

  17. Alfa Aesar Catalog, 2008/09, No. A16677 (Alfa Aeser, Ward Hill, MA., 2008).

  18. Referencia 12, págs. 752 a 755.

  19. Royals, E. E., Advanced Organic Chemistry, p. 434 (Prentice- Hall, Englewood Cliffs, N. J., 1961).

  20. Fuson, R. C., Advanced Organic Chemistry, p. 278 (J. Wiley, Nueva York, 1958).

  21. Smith, M. B. & March, J., March’s Advanced Organic Chemistry: reactions, mechanisms and structure, 6ª ed., pp. 95-98 (J. Wiley, Hoboken, NJ, 2007).

  22. Carey, F. A. & Sundberg, R. J., Advanced Organic Chemistry, 5a ed., p. 786 (Springer, Nueva York, 2007).

  23. Referencia 12, págs. 801 y 802.




2020     |     www.medigraphic.com