Collect. Czech. Chem. Commun.
2000, 65, 1791-1804
https://doi.org/10.1135/cccc20001791
Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene
Osman Çakmaka,*, Ismail Kahvecia, Íbrahim Demirtaşa, Tuncer Hökelekb and Keith Smithc
a Gaziosmanpaşa University, Faculty of Science, Department of Chemistry, 60100 Tokat, Turkey
b Hacettepe University, Department of Physics, 06532 Beytepe, Ankara, Turkey
c Department of Chemistry, University of Wales Swansea, Swansea SA2 8PP, U.K.
References
1a. K. D., Talapatra G. B., Tridibenta N. M.: Bull. Chem. Soc. Jpn. 1995, 68, 3331.
1b. S., Hanson D. M.: J. Phys. Chem. 1993, 97, 38.
1c. Y., Nelson M. C., Hanson D. M.: J. Chem. Phys. 1987, 86, 1586.
<https://doi.org/10.1063/1.452197>
1d. W. S., Zweil A. H.: J. Chem. Phys. 1983, 78, 2298.
<https://doi.org/10.1063/1.445084>
1e. J. C., Prasad P. N.: J. Phys. Chem. 1982, 86, 328.
<https://doi.org/10.1021/j100392a010>
1f. D. D., Millar D. P., Zewail A. H.: J. Chem. Phys. 1980, 72, 1187.
<https://doi.org/10.1063/1.439262>
1g. R. M., Johnson L. W., Klimcak C. M.: J. Chem. Phys. 1980, 73, 156.
<https://doi.org/10.1063/1.439899>
1h. J. J., Gooijer C., Velthorst N. H., Frei R. W.: Anal. Chem. 1982, 54, 891.
<https://doi.org/10.1021/ac00243a012>
1i. M., Sumiyoshi T., Miura N., Katayama M.: Bull. Chem. Soc. Jpn. 1982, 55, 2352.
<https://doi.org/10.1246/bcsj.55.2352>
2. For synthesis of α-naphthol from α-bromonaphthalene see: M. G., Mikheev Y. A., Guseva L. N.: Dokl. Akad. Nauk 1967, 176, 368.
3a. Encyclopedia of Chemical Technology, 3rd ed., Vol. 2, p. 309. Wiley, New York 1978.
3b. Krock F. W., Neeff R.: Eur. Pat. Appl. EP, 51, 783, 1982.
3c. Chem. Abstr. 1982, 97, 144615.
4a. R. G. R., Stewart O. J.: J. Chem. Soc. 1965, 4953.
<https://doi.org/10.1039/jr9650004953>
4b. For synthesis of aryl ethers see: Jones D.: Ph.D. Thesis. University College of Swansea, Swansea 1993.
5a. J.: Tetrahedron 1984, 40, 1433.
<https://doi.org/10.1016/S0040-4020(01)91791-0>
5b. B. G. R., Rennison S. C.: J. Chem. Soc. C 1969, 312.
<https://doi.org/10.1039/j39690000312>
6a. K., Sorensen J., Schaumburg K., Bechgaard K., Christensen J. B.: Synth. Commun. 1993, 23(13), 1905.
<https://doi.org/10.1080/00397919308011292>
6b. K., Sorensen J., Schaumburg K., Bechgaard K., Christensen J. B.: Synth. Met. 1993, 55–57, 2128.
6c. For synthesis oligothiophenes from 1,8-dibromnaphthalene by application of NiCl (dppp)-catalysed coupling with thienylmagnesium bromides see: M., Nakayama J., Hoshino M.: Tetrahedron 1993, 49, 3735.
<https://doi.org/10.1016/S0040-4020(01)90226-1>
7a. L. A.: Dokl. Akad. Nauk SSSR 1950, 17, 693.
7b. A. P., Belenkii L. I., Yanovskaya L. A.: Zh. Obshch. Khim. 1954, 24, 1265.
8. R. W., O'Reilly E. J.: J. Org. Chem. 1958, 23, 311.
<https://doi.org/10.1021/jo01096a614>
9. M., Satoh H., Yoshitomi S.: J. Org. Chem. 1988, 53, 2093.
<https://doi.org/10.1021/jo00244a046>
10a. M., Çakmak O., Hökelek T.: Tetrahedron 1992, 48, 3163.
<https://doi.org/10.1016/S0040-4020(01)92257-4>
10b. O., Balci M.: J. Org. Chem. 1992, 57, 6640.
10c. A., Taşkesenligil Y., Çakmak O., Abbasoglu R., Balci M.: J. Org. Chem. 1996, 61, 8297.
<https://doi.org/10.1021/jo960225l>
11. C.: Chem. Rev. (Washington, D. C.) 1948, 43, 271.
12. C. M., Bergamini A., Cozzi P. G., Papa A., Tagliavini E., Umani-Ronchi A.: Tetrahedron: Asymmetry 1997, 8, 895.
<https://doi.org/10.1016/S0957-4166(97)00061-X>
13a. Y., Yonezawa K., Saegusa T.: J. Org. Chem. 1974, 39, 2769.
<https://doi.org/10.1021/jo00932a020>
13b. S., Wehmeyer R. M., Forkner M. W., Rieke R. D.: J. Org. Chem. 1988, 53, 339.
<https://doi.org/10.1021/jo00237a022>
14. B. K.: J. Chem. Soc. 1933, 553.
<https://doi.org/10.1039/jr9330000553>
15. F., Lemmel L.: Ber. Dtsch. Chem. Ges. 1913, 46, 232.
<https://doi.org/10.1002/cber.19130460139>
16. J. B., Rubli H.: J. Chem. Soc. 1927, 3098.
<https://doi.org/10.1039/jr9270003098>
17. Ng. Ph.: Justus Liebigs Ann. Chem. 1944, 556, 1.
<https://doi.org/10.1002/jlac.19445560102>
18. B. R., Carlson G. H.: J. Am. Chem. Soc. 1942, 64, 2657.
<https://doi.org/10.1021/ja01263a038>
19. E. F., Linstead R. P.: J. Chem. Soc. 1936, 1739.
<https://doi.org/10.1039/jr9360001739>
20. J. V., Kischbaum G.: Ber. Dtsch. Chem. Ges. 1921, 54, 597.
<https://doi.org/10.1002/cber.19210540407>
21. A., Balci M., Hökelek T., Ülkü D., Büyükgüngör O.: Tetrahedron 1996, 50, 10555.
<https://doi.org/10.1016/S0040-4020(01)89596-X>
22a. T., Çakmak O., Balci M.: Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1990, 46, 1906.
<https://doi.org/10.1107/S0108270190000397>
22b. T., Çakmak O., Balci M.: Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 1672.
<https://doi.org/10.1107/S0108270190013622>
22c. M., Çakmak O., Hökelek T.: Tetrahedron 1992, 48, 3163.
<https://doi.org/10.1016/S0040-4020(01)92257-4>
23. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-145487. Copies of the data can be obtained free of charge on application to CCDC, e-mail: deposit@ccdc.cam.ac.uk.
24. U. G., Anderson R. G.: J. Org. Chem. 1957, 22, 1197.
<https://doi.org/10.1021/jo01361a018>
25a. A., Ziessel R.: Tetrahedron Lett. 1997, 38, 2471.
<https://doi.org/10.1016/S0040-4039(97)00412-7>
25b. M. B., Wege D.: Tetrahedron Lett. 1980, 21, 3831.
<https://doi.org/10.1016/0040-4039(80)80192-4>
25c. M., Tuihiji T., Nishimura J.: J. Org. Chem. 1993, 58, 7388.
<https://doi.org/10.1021/jo00078a016>
25d. G. A., Singh B. P., Liang G.: J. Org. Chem. 1984, 49, 2922.
<https://doi.org/10.1021/jo00190a016>
25e. T., Takahashi K., Takase K.: J. Chem. Soc., Perkin Trans. 1 1979, 889.
<https://doi.org/10.1039/p19790000889>
26a. M. S., Choudhary A. R.: Org. Prep. Proced. Int. 1989, 21, 359.
<https://doi.org/10.1080/00304948909356397>
26b. M., Brons G., Vaughn S. N., Katritzky A. R., Balasubramanian M., Greenhill J. V.: Energy Fuels 1993, 7589.
27. B. S., Jiang Quingping, Rho Taikyun, Pelletier S. W.: J. Org. Chem. 1994, 59, 8220.
<https://doi.org/10.1021/jo00105a046>
28. U. T., Sridhar M.: Tetrahedron Lett. 1994, 35, 1413.
<https://doi.org/10.1016/S0040-4039(00)76232-0>
29. M. A.: Can. J. Appl. Spectrosc. 1996, 41, 81.
30. M., Tsunetsugu J., Ebine S.: Bull. Chem. Soc. Jpn. 1976, 49, 2230.
<https://doi.org/10.1246/bcsj.49.2230>

