Halogenation of Benzocrown Ethers by Hypohalites in Aqueous Solutions

Sergei M. Pluzhnik-Gladyr

A.V. Bogatsky Physico-Chemical Institute of National Academy of Sciences of Ukraine, 65080 Odessa, Ukraine

Macroheterocycles 2012 5(4-5) 384-388

DOI: 10.6060/mhc2012.121103p

NaClO and NaBrO can be used as soft and selective reagents for chlorination and bromination of benzocrown ethers (BCE) in a water medium. The adjustment of pH in these processes enables the control of the resulting number of atoms of halogens in the aromatic fragment of BCE.

References

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1. Zhang J., Yang Sh., Liu W., Xue Q. Wear 1999, 236, 303-307.
http://dx.doi.org/10.1016/S0043-1648(99)00294-X

2. Ding Y.I., Qiu Ying Y.U., Guangming Y.Z.P. Journal Of Nuclear and Radiochemistry 1982, 4, 21-27.

3. Koenig B., Schofield E., Peter G.J., Bubenitschek P. J. Org. Chem. 1994, 59, 7142-7143.
http://dx.doi.org/10.1021/jo00102a049

4. Liao Yi., Zhuangyu Zhang, Hongwen Hu. Synth. Commun. 1995, 25, 595-601.
http://dx.doi.org/10.1080/00397919508011394

5. Kikukawa K., Takamura S., Hirayama H., Namiki H., Wada F., Matsuda T. Chemistry Letters 1980, 511-514.
http://dx.doi.org/10.1246/cl.1980.511

6. Kikukawa K., Abe A., Wada F., Matsuda T. Bull. Chem. Soc. Jap. 1983, 56, 961- 962.
http://dx.doi.org/10.1246/bcsj.56.961

7. Lukoyanov N.V., Vanikin G.I., Malygin V.V., Kal'chenko V.I., Parkhomenko N.A., Atamas' L.I., Pacheva L.M., Galenko T.G., Ivanova T.A., Panarin V.A., Raevskii O.A., Markovskii L.N. Pharmaceutical Chemistry Journal 1991, 25, 27-30.
http://dx.doi.org/10.1007/BF00766361

8. Takeshlta M., Irie M. J. Org. Chem. 1998, 63, 6643-6649.
http://dx.doi.org/10.1021/jo980290q

9. Shu-Qin Zhang, Yu-Ting Wang, Yu-Rong Tang. J. Appl. Polym. Sci. 2003, 90, 806- 809.
http://dx.doi.org/10.1002/app.12582

10. Klyatskaya S.V., Tretyakov E.V., Vasilevsky S.F. Arkivoc 2003, 13, 21-34.
http://dx.doi.org/10.3998/ark.5550190.0004.d04

11. Hyde E.M., Shaw B.L., Shepherd I. Dalton Trans. 1978, 1696-1705.
http://dx.doi.org/10.1039/dt9780001696

12. Takeshita M., Irie M. Tetrahedron Letters 1998, 39, 613-616.
http://dx.doi.org/10.1016/S0040-4039(97)10658-X

13. Erglis A. P., Brod I.I. USSR Pat. 1983, 1004379.

14. Sungeun Lee. Hongsuk Suh Bull. Korean Chem. Soc. 1999, 20, 991-997.

15. Gorbunova Y.G., Komarova Y.O., Demin S.V., Meshkov S.V., Tzivadze A.Y. Koord.Khim. 1997, 23, 553-556. [Russ. J. Coord. Chem. 1997, 23, 519].

16. Ungaro R., Haj B. El., Smid J. J. Amer. Chem. Soc. 1976, 98, 5198-5202.
http://dx.doi.org/10.1021/ja00433a024

17. Luboch E., Cygan A., Biernat J. F. Tetrahedron, 1990, 46, (7), 2461-2472.
http://dx.doi.org/10.1016/S0040-4020(01)82027-5

18. Kotlyar S.A., Pluzhnik-Gladyr S.M. Macroheterocycles 2008, 1, 85-89.

19. Pluzhnik-Gladyr S.M., Rakipov I.M., Kotlyar S.A. Bashkirskii Khimicheskii Zhurnal, 2008, 15, 63-66.

20. Pluzhnik-Gladyr S.M., Rakipov I.M., Kotlyar S.A. Macroheterocycles 2009, 2, 20-22.

21. Pluzhnik-Gladyr S.M., Rakipov I.M., Kotlyar S.A. Bashkirskii Khimicheskii Zhurnal 2008, 15, 72-75.

22. Yakshin V.V., Vilkova O.M., Kotlyar S.A., Kamalov G.L. Doklady AN Rossii 2007, 416, 662-665 (in Russ.).

23. Zlomanov V.P. Soros. Obrazov. Zh. 2001, 7, 46-51 (in Russ.).

24. Bogaschenko T., Basok S., Kulygina C., Lyapunov A., Lukyanenko N. Synthesis 2002, 2266-2270.
http://dx.doi.org/10.1055/s-2002-34853

25. Lukyanenko N. Janssen Chimica Acta 1992, 10, 12-18.

26. Schoniger W. Mikrochim. Acta 1955, 1, 123-129
http://dx.doi.org/10.1007/BF01220660

27. Jurd L. Australian J. Sci. Research 1949, 2A, 246.
http://dx.doi.org/10.1071/CH9490246

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Sergei M. Pluzhnik-Gladyr

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