Electroreduction of Organic Compounds, 34 [1]. Cathodic Dehalogenation of Chloroarenes with Electron-Donating Substituents

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 58, Issue 12, 2003, Pages 1187-1200

  Kranz, Olaf ^a   Voss, Jürgen ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Chloroarenes; Dehalogenation; Electrolysis

Indexed keywords

DEHALOGENATION; ELECTROLYSIS; PHENOLS;

CHLORINATED PHENOLS; CHLOROARENES; ELECTROCHEMICAL REDUCTIONS; ELECTRON-DONATING SUBSTITUENTS; GALVANOSTATIC CONDITIONS; HYDRODECHLORINATION; SUITABLE CONDITIONS; SUPPORTING ELECTROLYTE;

ELECTROLYTIC REDUCTION;

ANISOLE DERIVATIVE; CHLORINE DERIVATIVE; ELECTROLYTE; NITROFEN; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE DERIVATIVE;

ARTICLE; CHLORINATION; DEHALOGENATION; ELECTROCHEMISTRY; ELECTRODE; ELECTROLYSIS; ELECTRON TRANSPORT; POTENTIOMETRY; REDUCTION; SOIL POLLUTION; SOLVENT EFFECT; SUBSTITUTION REACTION;

EID: 0842287354     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2003-1206     Document Type: Article

References (67)

1. Part 33: D. Golinske, J. Voss, G. Adiwidjaja, Collect. Czech. Chem. Commun. 65, 862 (2000).
2. nd ed., Blackie, Chapman & Hall, London (1996).
3. nd ed., Blackie, Chapman & Hall, London (1996).
4. K. Ballschmiter, Pure Appl. Chem. 68, 1771 (1996).
5. K. Ballschmiter, R. Bacher, Dioxine: Chemie, Analytik, Vorkommen, Umweltverhalten und Toxikologie der halogenierten Dibenzo-p-dioxine und Dibenzofurane, Verlag Chemie, Weinheim (1996).
6. D. Petersen, M. Lemmrich, M. Altrogge, J. Voss, Z. Naturforsch. 45b, 1105 (1990).
7. J. Voss, M. Altrogge, D. Golinske, O. Kranz, D. Nünnecke, D. Petersen, E. Waller, Degradation of Chlorinated Arenes by Electroreduction, in R. Stegmann, G. Brunner, W. Calmano, G. Matz (eds.): Treatment of Contaminated Soil - Fundamentals, Analysis, Applications, p. 547-563, 651-652, Springer Verlag, Berlin, Heidelberg, New York (2001).
8. J. Voss, E. Waller, Elektrochemische Enthalogenierung von Mischungen chlorierter Aromaten in Ölmatrices, in R. Stegmann (ed.): Hamburger Berichte 10; Neue Techniken der Bodenreinigung, p. 65-73, Economica Verlag, Bonn (1996); E. Waller, Elektrochemische Enthalogenierung polychlorierter Naphthaline sowie Elektroreduktion monochlorierter Dibenzofurane, Dissertation, Universität Hamburg (1997); Shaker Verlag, Aachen (1998).
9. J. Voss, E. Waller, Elektrochemische Enthalogenierung von Mischungen chlorierter Aromaten in Ölmatrices, in R. Stegmann (ed.): Hamburger Berichte 10; Neue Techniken der Bodenreinigung, p. 65-73, Economica Verlag, Bonn (1996); E. Waller, Elektrochemische Enthalogenierung polychlorierter Naphthaline sowie Elektroreduktion monochlorierter Dibenzofurane, Dissertation, Universität Hamburg (1997); Shaker Verlag, Aachen (1998).
10. J. Voss, M. Altrogge, H. Wilkes, W. Francke, Z. Naturforsch. 46b, 400 (1991).
11. J. Voss, E. Waller, P. Kränke, J. Prakt. Chem. 340, 430 (1998).
12. D. Nünnecke, J. Voss, Acta Chem. Scand. 53, 824 (1999).
13. th ed., Georg Thieme Verlag, Stuttgart (1996).
14. L. N. Zanaveskin, V. A. Aver'yanov, Russ. Chem. Rev. 67, 713 (1998).
15. M. K. Anwer, D.B. Sherman, J.G. Roney, A. F. Spatola, J. Org. Chem. 54, 1284 (1989).
16. V. V. Grushin, H. Alper, Organometallics 10, 1620 (1991).
17. A. Marques, M. Selva, P. Tundo, J. Org. Chem. 59, 3830 (1994).
18. S. Rajagopal, A. F. Spatola, J. Org. Chem. 60, 1347 (1995).
19. H. Li, S. Liao, Y. Xu, D. Yu, Synth. Commun. 27, 829 (1997).
20. M. Lemmrich, Enthalogenierung von chlorierten Aromaten durch Elektroreduktion in Methanol, Diplomarbeit, Universität Hamburg (1989); J. Hoffmann, C-C-Verknüpfung an Anode und Kathode am Beispiel kleiner Ringe und langer Ketten, Dissertation, Universität Hamburg (1989).
21. M. Lemmrich, Enthalogenierung von chlorierten Aromaten durch Elektroreduktion in Methanol, Diplomarbeit, Universität Hamburg (1989); J. Hoffmann, C-C-Verknüpfung an Anode und Kathode am Beispiel kleiner Ringe und langer Ketten, Dissertation, Universität Hamburg (1989).
22. J. Gassmann, Theoretische und experimentelle Untersuchungen zur elektrochemischen Enthalogenierung aromatischer und aliphatischer Chlorverbindungen, Dissertation, Universität Hamburg (1995).
23. The electrochemical reduction of chlorinated anisoles in the aprotic solvent DMF has been studied by M. Kimura, H. Miyahara, N. Moritani, Y. Sawaki, J. Org. Chem. 55, 3897 (1990).
24. th Meeting of the Electrochemical Society, Los Angeles, CA, May 5-11, 1996. - Meeting Abstracts, The Electrochemical Society, Inc., Pennington, NJ, Vol. 96-1, 1242 (1996).
25. A. I. Tsyganok, I. Yamanaka, K. Otsuka, Chem. Lett. 303 (1998) and lit. cited therein.
26. H.-G. Franck, J. W. Stadelhofer, Industrial Aromatic Chemistry, p. 176-180, Springer Verlag, Berlin, Heidelberg, New York (1988).
27. D. Henschler, Angew. Chem. 106, 1997 (1994); Angew. Chem., Int. Ed. 33, 1920 (1994).
28. D. Henschler, Angew. Chem. 106, 1997 (1994); Angew. Chem., Int. Ed. 33, 1920 (1994).
29. S. Fetzner, F. Lingens, Microbiol. Rev. 58, 641 (1994).
30. S. Kremer, H. Anke, Fungi in Bioremediation, in T. Anke (ed.): Fungal Biotechnology, p. 275-295, Chapman & Hall, Weinheim (1997).
31. M. K. Anwer, A. F. Spatola, Tetrahedron Lett. 26, 1381 (1985).
32. T. Tsukinoki, T. Kakinami, Y. Iida, M. Ueno, Y. Ueno, T. Mashimo, H. Tsuzuki, M. Tashiro, J. Chem. Soc., Chem. Commun. 209 (1995).
33. C. Yang, C. U. Pittman jr., Synth. Commun. 28, 517 (1998).
34. F. Massicot, R. Schneider, Y. Fort, S. Illy-Cherrey, O. Tillement, Tetrahedron 56, 4765 (2000).
35. a) A. Sorokin, S. De Suzzoni-Dezard, D. Poullain, J.-P. Noël, B. Meunier, J. Am. Chem. Soc. 118, 7410 (1996).
36. b) A. Sorokin, B. Meunier, Chem. Eur. J. 2, 1308 (1996) and lit. cited therein.
37. S. Sen Gupta, M. Stadler, C. A. Noser, A. Ghosh, B. Steinhoff, D. Lenoir, C. P. Horwitz, K.-W. Schramm, T. C. Collins, Science 296, 326 (2002).
38. N. Bunce, S. G. Merica, J. Lipkowski, Chemosphere 35, 2719 (1997).
39. S. Taj, M. F. Ahmed, S. Sankarapapavinasam, J. Chem. Res. (S) 232 (1993).
40. U. Leffrang, K. Ebert, K. Flory, U. Galla, H. Schmieder, Sep. Sci. Technol. 30, 1883 (1995); Chem. Abstr. 122, 297988 (1995).
41. U. Leffrang, K. Ebert, K. Flory, U. Galla, H. Schmieder, Sep. Sci. Technol. 30, 1883 (1995); Chem. Abstr. 122, 297988 (1995).
42. B. J. Hwang, K. L. Lee, J. Appl. Electrochem. 26, 153 (1996).
43. A. M. Polcaro, S. Palmas, Ind. Eng. Chem. Res. 36, 1791 (1997).
44. S. K. Johnson, L. L. Houk, J. Feng, R. S. Houk, D. C. Johnson, Environ. Sci. Technol. 33, 2638 (1999); Chem. Abstr. 131, 91919 (1999).
45. S. K. Johnson, L. L. Houk, J. Feng, R. S. Houk, D. C. Johnson, Environ. Sci. Technol. 33, 2638 (1999); Chem. Abstr. 131, 91919 (1999).
46. N. C. Ross, R. A. Spackman, M. L. Hitchman, P. White, J. Appl. Electrochem. 27, 51 (1997).
47. D. Schmal, P. J. van Duin, A. M. C. P. de Jong, Electrochemical Dehalogenation of Toxic Organic Compounds in Industrial Waste Water, in A. Winsel, D. Behrens (eds.): Elektrochemie in Energie-und Umwelttechnik, Dechema-Monographien, Vol. 124, p. 241-247, Verlag Chemie, Weinheim (1991).
48. G. Battistuzzi Gavioli, M. Borsari, C. Fontanesi, J. Chem. Soc., Faraday Trans. 89, 3931 (1993). Pentachlorophenol (32) exhibits three irreversible reduction steps at -1.3 V, -1.7 V and -2.1 V.
49. K. P. Scharwächter, O. Kranz, J. Voss, W. A. König, J. Microcolumn Separations 12, 68 (2000).
50. W. Zumach, Chem. Unserer Zeit 37, 127, 2003.
51. a) A. Riebel, H. Beitz, Nachrichtenbl. Deut. Pflanzenschutzd. 46, 77 (1994).
52. b) S. Schmidt, Biodegradation of Diaryl Ether Pesticides, in R.-M. Wittich (ed.): Biodegradation of Dioxins and Furans, chapt. 8, p. 229-281, Springer Verlag, Berlin, Heidelberg, New York, and Landes Bioscience, Austin, TX, USA (1998).
53. th ed., pp. 204, 210, 567, Johann Ambrosius Barth Verlag, Leipzig (1993).
54. H. C. Brimelow, R. L. Jones, T. P. Metcalfe, J. Chem. Soc. 1208 (1951).
55. H. A. Muathen, Tetrahedron 52, 8863 (1996).
56. O. Silberrad, J. Chem. Soc. 127, 2677 (1925).
57. J. S. Morley, J. Chem. Soc. 1414 (1961).
58. S. J. Branch, B. Jones, J. Chem. Soc. 2921 (1955).
59. C. Heathcock, Can. J. Chem. 40, 1865 (1962).
60. B. Jones, J. Chem. Soc. 145, 430 (1943).
61. K. Tatsuta, M. Itoh, Tetrahedron Lett. 34, 8443 (1993).
62. A. Burger, E. L. Wilson, C. O. Brindley, F. Bernheim, J. Am. Chem. Soc. 67, 1416 (1945).
63. S. N. Chatfield, M. Y. Croft, T. Dang, E. J. Murby, G. Y. F. Yu, R. J. Wells, Anal. Chem. 67, 945 (1995).
64. D. C. DeJongh, D. A. Brent, R. Y. Van Fossen, J. Org. Chem. 36, 1469 (1971).
65. R. Howe, J. Chem. Soc. C, 478 (1966).
66. M. T. M. Tulp, G. Sundström, O. Hutzinger, Chemosphere, 5, 425 (1976); D. R. Knapp, Handbook of Analytical Derivatization Reactions, p. 49, J. Wiley & Sons, New York (1979).
67. M. T. M. Tulp, G. Sundström, O. Hutzinger, Chemosphere, 5, 425 (1976); D. R. Knapp, Handbook of Analytical Derivatization Reactions, p. 49, J. Wiley & Sons, New York (1979).