A stable carbene as π-acceptor. Electrochemical reduction to the radical anion

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2833-2836

  Enders, Dieter ^a   Breuer, Klaus ^a   Raabe, Gerhard ^a   Simonet, Jacques ^b   Ghanimi, Ahmed ^b   Stegmann, Hartmut B ^c   Teles, J Henrique ^d  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITY OF TÜBINGEN   (Germany)

^d BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; RADICAL;

ARTICLE; CALCULATION; CYCLIC POTENTIOMETRY; DRUG STABILITY; DRUG STRUCTURE; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; THEORY;

EID: 0030902972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00493-0     Document Type: Article

References (16)

1. (a) Arduengo III, A. J.; Harlow, R. L.; Kline, M.; J. Am. Chem. Soc. 1991, 113, 361.
2. (b) Arduengo III, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M.; ibid. 1992, 114, 5530.
3. (c) For a comprehensive review of the chemistry of stable carbenes see: Regitz, M. Angew. Chem. 1996, 108, 791; Angew. Chem. Int. Ed. Engl. 1996, 35, 725.
4. (c) For a comprehensive review of the chemistry of stable carbenes see: Regitz, M. Angew. Chem. 1996, 108, 791; Angew. Chem. Int. Ed. Engl. 1996, 35, 725.
5. (a) Shi, Z.; Thummel, R. P. Tetrahedron Lett. 1995, 36, 2741.
6. (b) Shi, Z.; Goulle, V.; Thummel, R. P. Tetrahedron Lett. 1996, 37, 2357.
7. (a) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119; Angew. Chem. Int. Ed. Engl. 1995, 34, 1021.
8. (a) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119; Angew. Chem. Int. Ed. Engl. 1995, 34, 1021.
9. (b) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Liebigs Ann. Chem. 1996, 2019.
10. Enders, D.; Breuer, K.; Teles, J. H.; Ebel, K. J. Prakt. Chem. 1997, submitted.
11. (a) Raabe, G.; Breuer, K.; Enders, D.; Teles, J. H. Z. Naturforsch. 1996, 51a, 95.
12. (b) Heinemann, C.; Thiel, W. Chem. Phys.
13. (c) Sauers, R. R. Tetrahedron Lett. 1996, 37, 149.
14. (d) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
15. (e) Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039.
16. At r.t. the generated radical anion reacted fast with acidic impurities (e. g. moisture) giving a two electron transfer process. After several sweeps, the surrounding of the working electrode was practically free of these acidic contaminants and a clean, reversible one electron step was observed.