Reductive bond cleavage of chloro-substituted 10-methyl- tribenzotriquinacenes: Transition between concerted and stepwise mechanisms

Electrochimica Acta

Volumn 51, Issue 27, 2006, Pages 6069-6075

  Jaworski, Jan S ^a   Cembor, Marek ^a   Kuck, Dietmar ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b BIELEFELD UNIVERSITY   (Germany)

Author keywords

Bond cleavage; Centropolyindanes; Concerted mechanism; Cyclic voltammetry; Radical anions

Indexed keywords

CHEMICAL BONDS; CYCLIC VOLTAMMETRY; DISSOCIATION; ELECTRON TRANSITIONS; SUBSTITUTION REACTIONS;

BOND CLEAVAGE; CENTROPOLYINDANES; CONCERTED MECHANISM; HOMOLYTIC DISSOCIATION ENERGY; RADICAL ANIONS;

HYDROCARBONS;

EID: 33747091924     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2005.11.050     Document Type: Article

References (44)

1. Kuck D. Top. Curr. Chem. 196 (1998) 167
2. Kuck D. Synlett (1996) 949
3. Kuck D. Liebigs Ann./Recueil (1997) 1043
4. Kuck D. Pure Appl. Chem. 78 (2006) 749
5. Kuck D., and Schuster A. Angew. Chem. 100 (1988) 1222
6. Kuck D., and Schuster A. Angew. Chem. Int., Ed. Engl. 27 (1988) 1192
7. Kuck D., Schuster A., Paisdor B., and Gestmann D. J. Chem. Soc., Perkin Trans. 1 (1995) 721
8. Kuck D. Angew. Chem. 96 (1984) 515
9. Kuck D. Angew. Chem. Int. Ed. Engl. 23 (1984) 508
10. Kuck D., Lindenthal T., and Schuster A. Chem. Ber. 125 (1992) 1449
11. Kuck D., Schuster A., Ohlhorst B., Sinnwell V., and de Meijere A. Angew. Chem. 101 (1989) 626
12. Kuck D., Schuster A., Ohlhorst B., Sinnwell V., and de Meijere A. Angew. Chem., Int. Ed. Engl. 28 (1989) 595
13. Kuck D., Neumann E., and Schuster A. Chem. Ber. 217 (1994) 151
14. Schuster A., and Kuck D. Angew. Chem. 103 (1991) 1717
15. Schuster A., and Kuck D. Angew. Chem., Int. Ed. Engl. 30 (1991) 1699
16. Kuck D., Schuster A., Fusco C., Fiorentino M., and Curci R. J. Am. Chem. Soc. 116 (1994) 2375
17. Kuck D., Schuster A., Krause R.A., Tellenbröker J., Exner C.P., Penk M., Bögge H., and Müller A. Tetrahedron 57 (2001) 3587
18. Tellenbröker J., and Kuck D. Angew. Chem. 111 (1999) 1000
19. Tellenbröker J., and Kuck D. Angew. Chem., Int. Ed. Engl. 38 (1999) 919
20. Cao X.P., Barth D., and Kuck D. Eur. J. Org. Chem. 16 (2005) 3482
21. Jaworski J.S., and Kuck D. Pol. J. Chem. 78 (2004) 1597
22. Savéant J.M. Adv. Phys. Org. Chem. 26 (1990) 1
23. Savéant J.M. Adv. Phys. Org. Chem. 35 (2000) 117
24. Grimshaw J. Electrochemical Reactions and Mechanisms in Organic Chemistry (2000), Elsevier, Amsterdam p. 89
25. Andrieux C.P., Savéant J.M., and Su K.B. J. Phys. Chem. 90 (1986) 3815
26. Andrieux C.P., Le Gorande A., and Savéant J.M. J. Am. Chem. Soc. 114 (1992) 6892
27. Andrieux C.P., Differding E., Robert M., and Savéant J.M. J. Am. Chem. Soc. 115 (1993) 6592
28. Andrieux C.P., Robert M., Saeva F.D., and Savéant J.M. J. Am. Chem. Soc. 116 (1994) 7864
29. Andrieux C.P., Savéant J.M., Tallec A., Tardivel R., and Tardy C. J. Am. Chem. Soc. 119 (1997) 2420
30. Andrieux C.P., Savéant J.M., and Tardy C. J. Am. Chem. Soc. 119 (1997) 11546
31. Costentin C., Hapiot P., Médebielle M., and Savéant J.M. J. Am. Chem. Soc. 121 (1999) 4451
32. Pause L., Robert M., and Savéant J.M. J. Am. Chem. Soc. 121 (1999) 7158
33. Antonello S., and Maran F. J. Am. Chem. Soc. 119 (1997) 12595
34. Antonello S., and Maran F. J. Am. Chem. Soc. 121 (1999) 9668
35. Bellomunno C., Bonanomi D., Falciola L., Longhi M., Mussini P.R., Doubova L.M., and Di Silvestro G. Electrochim. Acta 50 (2005) 2331
36. Galus Z. Fundamentals of Electrochemical Analysis. second ed. (1994), Ellis Horwood and PWN, New York and Warsaw p. 299
37. Severin M.G., Farnia G., Vianello E., and Arévalo M.C. J. Electroanal. Chem. 251 (1988) 369
38. Andrieux C.P., Gallardo I., Savéant J.M., and Su K.B. J. Am. Chem. Soc. 108 (1986) 638
39. M'Halla F., Pinson J., and Savéant J.M. J. Am. Chem. Soc. 102 (1980) 4120
40. Jensen H., and Daasbjerg K. Acta Chem. Scand. 52 (1998) 1151
41. Jaworski J.S., Cembor M., and Orlik M. J. Electroanal. Chem. 582 (2005) 165
42. Savéant J.M. J. Am. Chem. Soc. 109 (1987) 6788
43. Savéant J.M. J. Am. Chem. Soc. 114 (1992) 10595
44. Luo Y.R. Handbook of Bond Dissociation Energies in Organic Compounds (2003), CRC Press, Boca Raton p. 142