Electrochemically induced Favorsky rearrangement: Transformations of dialkyl ketones into α,β-unsaturated carboxylic esters

Russian Chemical Bulletin

Volumn 52, Issue 4, 2003, Pages 998-1002

  Elinson, M N ^a   Feducovich, S K ^a   Zaimovskaya, T A ^b   Dorofeev, A S ^a   Vereshchagin, A N ^a   Nikishin, G I ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b TOPCHIEV INSTITUTE OF PETROCHEMICAL SYNTHESIS   (Russian Federation)

Author keywords

Dialkyl ketones; Electrochemical oxidation; Electrolysis; Mediator systems; Unsaturated carboxylic esters

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; KETONE;

ARTICLE; ELECTROCHEMISTRY; ELECTROLYSIS; FAVORSKII REARRANGEMENT; OXIDATION;

EID: 0037745013     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1024481216415     Document Type: Article

References (25)

1. S. K. Chakrabartty, in Oxidation in Organic Chemistry, Pt. C, Ed. W. S. Trahanovsky, Academic Press, New York, 1978, p. 343.
2. R. T. Arnold, R. Buckles, and J. Stoltenberg, J. Am. Chem. Soc., 1944, 66, 208.
3. R. Levine and J. R. Stephens, J. Am. Chem. Soc., 1950, 72, 1642.
4. R. C. Fuson and B. A. Bull, Chem. Rev., 1934, 15, 275.
5. J. Grimshow, Electrochemical Reactions and Mechanisms in Organic Chemistry, Elsevier, Amsterdam, 2000.
6. Organic Electrochemistry, Ed. H. Lund, Marcel Dekker, Inc., New York, 2000.
7. W. E. Bradt and N. J. Opp, Trans. Electrochem. Soc., 1931, 59, 237.
8. M. Yokoyama, Bull. Chem. Soc. Jpn., 1933, 8, 71.
9. F. Pirrone, Gazz. Chim. Ital., 1936, 66, 244.
10. J. W. Shipley and M. T. Rogers, Can. J. Res., 1939, 17B, 147.
11. J. Y. Becker, L. R. Byrd, L. L. Miller, and Y.-H. So, J. Am. Chem. Soc., 1975, 97, 853.
12. C. B. Campbell and D. Pletcher, Electrochim. Acta, 1978, 23, 953.
13. C. Rappe, in The Chemistry of the Carbon-Halogen Bond, Ed. S. Patai, Wiley, New York, 1973, Pt. 2, p. 1071.
14. G. I. Nikishin, M. N. Elinson, and I. V. Makhova, Angew. Chem., 1988, 100, 1716.
15. M. N. Elinson, I. V. Makhova, and G. I. Nikishin, Tetrahedron, 1991, 47, 895.
16. T. Shono, Y. Matsumura, K. Inoe, and F. Iwasaki, J. Chem. Soc., Perkin Trans, 1, 1986, 73.
17. F. Barba, M. N. Elinson, J. Escudero, and S. K. Feducovich, Tetrahedron, 1997, 53, 4427.
18. M. N. Elinson, S. K. Feducovich, A. S. Dorofeev, A. N. Vereshchagin, and G. I. Nikishin, Tetrahedron, 2000, 56, 9999.
19. F. Barba, M. N. Elinson, J. Escudero, M. Guirado, and S. K. Feducovich, Electrochim. Acta, 1998, 43, 973.
20. H. C. Brown, J. Chem. Soc., 1956, 1248.
21. H. O. Krabbenhoft, J. Org. Chem., 1979, 44, 4285.
22. J. Palaty and F. S. Abbott, J. Med. Chem., 1995, 38, 3406.
23. S. Derien, E. Dunach, and J. Perichon, J. Am. Chem. Soc., 1991, 113; 8447.
24. T. K. Chumachenko, G. L. Kamalov, A. V. Bogatskii, and A. I. Gren', Zh. Org. Khim., 1970, 40, 846 [J. Org. Chem. USSR, 1970, 40 (Engl. Transl.)].
25. T. K. Chumachenko, G. L. Kamalov, A. V. Bogatskii, and A. I. Gren', Zh. Org. Khim., 1970, 40, 846 [J. Org. Chem. USSR, 1970, 40 (Engl. Transl.)].