A Short-Lived Radical Dication as a Key Intermediate in the Rearrangement of a Persistent Cation: The Oxidative Cyclization of 2,2-Dimesityl-1-(4-N,N-dimethylaminophenyl)ethenol

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 4, 1997, Pages 392-395

  Schmittel, Michael ^a   Langels, Anja ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Cyclic voltammetry; Enols; Oxidations; Radical ions

Indexed keywords

EID: 0031001578     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199703921     Document Type: Article

References (27)

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13. 3), 5.05 (s, 1 H, OH), 6.49 (d, 2 H. J = 9.0 Hz, Ar-H), 6.67 (s, 2 H, Mes-H), 6.87 (s, 2H, Mes-H), 7.20 (d, 2H, J = 9.0 Hz, Ar-H).
14. 1/2 = 0.39 V vs SCE).
15. 3), 6.60 (d, 2H, J = 9.2 Hz, Ar-H), 6.71 (s, 1H, 5-Bf-H), 6.96 (s, 2H, Mes-H), 7.39 (d, 2H, J = 9.2 Hz, Ar-H). Bf = benzofuran.
16. K. Izutsu, Acid-Base Dissociation Constants in Dipolar Aprotic Solvents, Blackwell, Oxford, 1990.
17. ... N bond was reported: U. Pindur, Arch. Pharm. 1980, 313, 301-306.
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19. -1: M. Schmittel, M. Röck, unpublished results.
20. pc = 0.69 V increased with the number of cycles.
21. 2+.
22. 2+, thus explaining the high peak intensity of wave III.
23. 2+ + B is followed by quantitative protonation of B.
24. -1 no sign of reversibility was found in the CV experiment.
25. M. F. Marcus, M. D. Hawley, J. Electroanal. Chem. 1968, 18, 175-183.
26. a) B. Speiser, A. Rieker, Electrochim. Acta 1978, 23, 983-989;
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