Cyclopropane formation by electroreductive coupling of activated olefins and gem-polyhalo compounds

Tetrahedron

Volumn 54, Issue 13, 1998, Pages 3207-3218

  Léonel, Eric ^a   Paugam, Jean Paul ^a   Condon Gueugnot, Sylvie ^a   Nédélec, Jean Yves ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANION; CYCLOPROPANE; POLYHALO DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL REACTION; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032568354     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00059-3     Document Type: Article

References (25)

1. 1. (a) Doering, W. von E.; Buttery, R. G.; Laughlin, R. G.; Chaudhuri, N. J. Am. Chem. Soc., 1956, 78, 3224.
2. (b) Carruthers, W. Some modern methods of organic synthesis; Third edition, CUP, Cambridge, 1986; pp. 91-92.
3. (c) Doering, W. von E.; Hoffmann, A. K. J. Am. Chem. Soc., 1954, 76, 6162-6165.
4. (d) Makosza, M; Wawrzyniewicz, M. Tetrahedron Lett., 1969, 4659-4662.
5. (e) Regen, S. L.; Singh, A. J. Org. Chem., 1982, 47, 1587-1588.
6. (f) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc., 1959, 81, 4256-4264.
7. (g) Simmons, H. E.; Cairns, T. L.; Vladuchick, S.A.; Hoiness, C. M. Organic Reactions; John Wiley, New York, London, Sydney, Toronto, 1973, 20, pp. 1-131.
8. 2. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1965, 87, 1353-1364.
9. 3. Kanaï, H.; Hiraki, N.; Iida, S. Bull Chem. Soc. Jpn., 1983, 56, 1025-1029. Kanaï, H.; Nishiguchi, Y.; Matsuda, H. Bull. Chem. Soc. Jpn., 1983, 56, 1592-1597.
10. 3. Kanaï, H.; Hiraki, N.; Iida, S. Bull Chem. Soc. Jpn., 1983, 56, 1025-1029. Kanaï, H.; Nishiguchi, Y.; Matsuda, H. Bull. Chem. Soc. Jpn., 1983, 56, 1592-1597.
11. 4. Baizer, M. M.; Chruma, J. L. J. Org. Chem., 1972, 37, 1951-1960.
12. 5. Le Menn, J. C.; Tallec, A.; Sarrazin, J. Can. J. Chem., 1991, 69, 761-767.
13. 6. (a) Lu, Y.-W.; Nédélec, J.-Y.; Folest, J.-C.; Périchon, J. J. Org. Chem., 1990, 55, 2503-2507.
14. (b) Lachaise, I.; Lu, Y. W.; Nédélec, J. Y.; Périchon J. Res. Chem. Interm., 1991, 15, 253-260.
15. 7. Duchek, P.; Ponec, R.; Chvalowsky, V. J. Organomet. Chem., 1984, 271, 101-106.
16. 8. Kurosawa, K.; Obara, H. Bull. Chem. Soc. Jpn., 1966, 39, 525-530.
17. 9. (a) Petrovich, J. P.; Baizer, M. M.; Ort, M. R. J. Electrochem. Soc., 1969, 116, 743-756.
18. (b) Puglisi, V. J.; Bard, A. J. J. Electrochem. Soc., 1972, 119, 829-833.
19. (c) Lamy, E.; Nadjo, L.; Saveant, J. M. J. Electroanal. Chem., 1973, 42, 189-221.
20. (d) Degrand, C.; Lund, H. Nouv. J. Chim., 1977, 1, 35-39.
21. 10. (a) Walser, P.; Renold P.; N' Goka, V.; Hosseinzadeh, F.; Tamm, C. Helv. Chim. Acta, 1991, 74, 1941-1952.
22. (b) Jones, W. M. J. Am. Chem. Soc., 1959, 81, 5153-5156.
23. 11. Bellesia, F.; Ghelfi, F.; Pagnoni, U. M.; Pinetti, A. J. Chem. Res. (S), 1989, 108-109.
24. 12. (a) Cuppen, Th. J. H. M.; Laarhoven, W. H. J. Am. Chem. Soc., 1972, 94, 5914-5915.
25. (b) Ito, S.; Hirata, Y. Bull Chem. Soc. Jpn. 1977, 50, 1813-1820.