Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5632-5636

  Wu, Xin ^a   Davis, Anthony P ^a   Fry, Albert J ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38349089000     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7026416     Document Type: Article

References (24)

1. This paper is dedicated to the memory of Yoshihiro Matsumura.
2. Bertram, J.; Fleischmann, M.; Pletcher, D. Tetrahedron Lett. 1971, 12, 349.
3. Möller, K.-C.; Schäfer, H. J. Electrochim. Acta 1996, 42, 1971.
4. (a) Steckhan, E. J. Am. Chem. Soc. 1978, 100, 3526.
5. (b) Steckhan, E.; Schäfer, H. J. Angew. Chem., Int. Ed. Engl. 1974, 13, 472.
6. (c) Bäumer, U.-St.; Schäfer, H. J. Electrochim. Acta 1997, 42, 1971.
7. Möller, K.-G; Schäfer, H. J. Electrochim. Acta 1997, 42, 1971.
8. (a) O'Connor, J. J.; Pearl, I. A. J. Electrochem. Soc. 1964, 111, 335.
9. (b) Svanhom, U.; Ronlan, A.; Parker, V. D. J. Am. Chem. Soc. 1974, 96, 5108.
10. Halas, S. M.; Okyne, K.; Fry, A. J. Electrochim. Acta 2003, 48, 1837.
11. (a) Steckhan, E. Top. Curr. Chem. 1987, 142, 1.
12. (b) Simonet, J.; Pilard, J.-F. Organic Electrochemistry; Lund, H., Hammerich, O., Eds.; Dekker: New York, 2001; p 1164 ff.
13. (c) Torii, S. Organic Electrochemistry; Schäfer, H. J., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15, pp 503-505.
14. Simonet, J.; Pilard, J.-F. Organic Electrochemistry; Lund, H., Hammerich, O., Eds.; Dekker: New York, 2001; Chapter 29, pp 1183-1185.
15. Bäumer, U.-St.; Schäfer, H. J. Electrochim. Acta 2003, 48, 489.
16. Bäumer, U.-St.; Schäfer, H. J. J. Appl. Electrochem. 2005, 35, 1283.
17. Steckhan, E.; Kandzia, C. Synlett 1992, 139.
18. (a) Schmidt, W.; Steckhan, E. Chem. Ber. 1980, 113, 577.
19. (b) Steckhan, E. Angew. Chem., Int. Ed. Engl. 1986, 25, 683.
20. Wu, X.; Dube, M. A.; Fry, A. J. Tetrahedron Lett. 2006, 47, 7667.
21. (a) McMurry, J. E.; Fleming, M. P. J. Am. Chem. Soc. 1974, 96, 4708.
22. (b) McMurry, J. E. Acc. Chem. Res. 1974, 7, 281.
23. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
24. A reviewer suggested that it would be experimentally simpler to carry the reactions out at constant current. Under constant current conditions, several as yet unidentified low-yield byproducts accompany the desired aldehydes. The reasons for this behavior are being investigated.