Electrochemical chlorination of azulene derivatives. Insight into the mechanism of anodic oxidative chlorination

Electrochimica Acta

Volumn 52, Issue 3, 2006, Pages 794-803

  Ungureanu, Eleonora M ^a   Razus, Alexandru C ^b   Birzan, Liviu ^b   Buica, George ^a   Cretu, Mariana ^a   Cristian, Enache ^b  

^a UNIVERSITY POLITEHNICA OF BUCHAREST   (Romania)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

Author keywords

Azulenes; Controlled potential electrolysis; Cyclic voltammetry; Electrochemical halogenation; Reaction mechanism

Indexed keywords

AZULENES; CONTROLLED POTENTIAL ELECTROLYSIS; ELECTROCHEMICAL HALOGENATION; REACTION MECHANISM;

CHLORINATION; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTROLYSIS; HALOGEN COMPOUNDS; ION EXCHANGE; OXIDATION;

OLEFINS;

EID: 33749620369     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2006.06.012     Document Type: Article

References (28)

1. Ellis S.R., Pletcher D., Brooks W.N., and Healy K.P. J. Appl. Electrochem. 13 (1983) 735
2. Gourcy J., and Simonet J. Electrochim. Acta 24 (1979) 1039
3. Fernández L., Márquez O.P., Márquez J., and Velásquez W. Rev. Téc. Ing. Univ. Zulia. 25 (2002) 108. from http://www.sielo.org.ve/scielo.php?pid=S0254-07702002000200006&scrip t=sci-arttext
4. Weinberg N.L. Technique of Electroorganic Synthesis, Part II vol. V (1975), Wiley/Interscience, New York p. 690
5. Forsyth S.R., and Pletcher D. J. Appl. Electrochem. 17 (1987) 905
6. Appelbaum L., Danovich D., LAzanes G., Michman M., and Oron M. J. Electroanal. Chem. 499 (2001) 39
7. Kurihara T., Suzuki T., Wakabayashi H., Ishikawa S., Shindo K., Shimada Y., Chiba H., Miyashi T., Yasunami M., and Nozoe T. Bull. Chem. Soc. Jpn. 69 (1996) 2003
8. Anderson A.G., Nelson J.A., and Tazuma J.J. J. Am. Chem. Soc. 75 (1953) 4980
9. Hapner K., and Bernhard C. Ann. Chem. 625 (1959) 108
10. Treibs W., and Neupert H.J. J. Hiebsch, Chem. Ber. 92 (1959) 1226
11. Anderson A.G., Scotoni R., Cowles E.J., and Fritz C.G. J. Org. Chem. 22 (1957) 1193
12. L. Birzan, Ph.D. dissertation, Bucharest, 2000
13. Razus A.C., Birzan L., Razus S.A., and Horga V. Rev. Roum. Chim. 44 3 (1999) 235
14. Anderson A.G., and Steckler B.M. J. Am. Chem. Soc. 81 (1959) 4941
15. Anderson A.G., and McDonald R.N. J. Am. Chem. Soc. 81 (1959) 5669
16. Ueno T., Toda H., Yasunami M., and Yoshifuji M. Bull. Chem. Soc. Jpn. 69 (1996) 1645
17. Ungureanu E.M., Razus A.C., Birzan L., Buica G., and Cretu M. Ovidius Univ. Ann. Chem. 16 2 (2005) 265
18. Ungureanu E.M., Razus A., Birzan L., Buica G., and Cretu M. Univ. Polytech. Bucharest Sci. Bull. 65 2 (2005) 3
19. Ungureanu E.M., Razus A., Birzan L., Buica G., and Cretu M. Univ. Polytech. Bucharest Sci. Bull. 67 3 (2005) 81
20. K.P. Zeller, Methoden der organischen Chemie-Houben-Weil, vol. V/2c, Georg Thieme Verlag, Stuttgart, p. 320.
21. Weinberg N.L. Technique of electroorganic synthesis, Part II vol.V (1975), Wiley/Interscience, NY p. 898
22. Mastragostino M., Casalbore G., and Valcher S. Electroanal.Chem. Interfacial Electrochem. 56 (1974) 117
23. J.J.P. Stewart, MOPAC 6.0 QPCE No. 455, 1989.
24. Sumida T., Kikuchi S., and Imafuku K. Synth. Commun. 34 23 (2004) 4273-4284
25. Pross A. J. Am. Chem. Soc. 108 (1986) 3537
26. Eberson L., Blum Z., Helgne B., and Nyberg K. Tetrahedron 34 (1978) 731
27. Razus A.C. J. Chem. Soc., Perkin Trans. 1 (2000) 981-988
28. Eberson L., Gonzalez-Luque R., Merchan M., Radner F., Ross B.O., and Shaik S. J. Chem. Soc., Perkin Trans. 2 (1997) 463