An environmentally friendly synthesis of functionalized indanes using electrochemical cyclization of ortho-halo-substituted homoallyl ethers and esters

Synlett

Volumn , Issue 13, 2006, Pages 2021-2026

  Olivero, Sandra ^a   Perriot, Rodolphe ^a   Duñach, Elisabet ^a   Baru, Ashvin R ^b   Bell, Eric D ^b   Mohan, Ram S ^b  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

^b ILLINOIS WESLEYAN UNIVERSITY   (United States)

Author keywords

Bismuth; Electrochemical cyclization; Homoallyl ethers; Indanes; Ni(II) cyclam

Indexed keywords

1 BENZYLOXY 3 METHYLINDANE; 1,4,8,11 TETRAMETHYL 1,4,8,11 TETRAAZACYCLOTETRADECANE; ACETAL DERIVATIVE; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; BISMUTH; CYCLAM; ESTER DERIVATIVE; ETHER DERIVATIVE; ETHOXY 3 METHYL INDANE; ETHYLOXY 3,3 DIMETHYLINDANE; HOMOALLYL ETHER DERIVATIVE; INDAN DERIVATIVE; METHOXY 3 METHYLINDANE; METHYLINDYL ACETATE; TETRADECANE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROLYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33748264678     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948182     Document Type: Article

References (33)

1. (a) Giese, B. In Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
2. (b) Stork, G. In Radical-Mediated Cyclization Processes - A Goal for Synthetic Efficiency; Bartmann, W.; Trost, B. M., Eds.; Verlag Chemie: Basel, 1984.
3. (a) Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P. P. Tetrahedron 2004, 60, 6239.
4. (b) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley and Sons: London, 2004.
5. Duñach, E.; Franco, D.; Olivero, S. Eur. J. Org. Chem. 2003, 1605.
6. Olivero, S.; Rolland, J.-P.; Duñach, E. Organometallics 1998, 17, 3747.
7. (a) Hong, B.-C.; Sarshar, S. Org. Prep. Proced. Int. 1999, 1, 1.
8. (b) Wickens, P.; Cantin, L.-D.; Chuang, C.-Y.; Dai, M.; Hentemann, M. F.; Kumarasinghe, E.; Liang, S. X.; Lowe, D. B.; Shelekhin, T. E.; Wang, Y.; Zhang, C.; Zhang, H.-J.; Zhao, Q. PCT Int. Appl., WO 2004011446, 2004.
9. (c) Sekiguchi, T.; Nakagawa, S.; Fujikura, Y. JP 03044337, 1991.
10. (d) Meakins, S. E.; Motion, K. R. Eur. Pat. Appl., EP 393742, 1990.
11. (e) Frank, W. C. USA, US 93-79008, 1994.
12. (f) Ohnuma, H.; Fujikura, Y.; Fujita; M.; Toi, N. Eur. Pat. Appl., EP 385497, 1990.
13. (g) Sprecker, M. A.; Weiss, R. A.; Belko, R. P.; Molner, E. A. USA, US 6342612, 2002.
14. (a) Wickens, P.; Cantin, L.-D.; Chuang, C.-Y.; Dai, M.; Hentemann, M. F.; Kumarasinghe, E.; Liang, S. X.; Lowe, D. B.; Shelekhin, T. E.; Wang, Y.; Zhang, C.; Zhang, H.-J.; Zhao, Q. PCT Int. Appl., WO 2004011446, 2004.
15. (b) Sekiguchi, T.; Nakagawa, S.; Fujikura, Y. JP 03044337, 1991.
16. (c) Meakins, S. E.; Motion, K. R. Eur. Pat. Appl., EP 393742, 1990.
17. (d) Frank, W. C. USA, US 93-79008, 1994.
18. Anzalone, P. W.; Baru, A. R.; Danielson, E. M.; Hayes, P. D.; Nguyen, M. P.; Panico, A. F.; Smith, R. C.; Mohan, R. S. J. Org. Chem. 2005, 70, 2091.
19. (a) Reglinski, J. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: New York, 1998, 403-440.
20. (b) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001.
21. (c) Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.
22. (d) Antoniotti, S. Synlett 2003, 1566.
23. (e) Gaspard-Iloughmane, H.; Le Roux, C. Eur. J. Org. Chem. 2004, 2517.
24. Bosnich, B.; Tobe, M. L.; Webb, G. A. Inorg. Chem. 1965, 4, 1109.
25. Gosden, C.; Healy, K. P.; Pletcher, D. J. Chem. Soc., Dalton Trans. 1978, 8, 972.
26. Duñach, E.; Esteves, A. P.; Medeiros, M. J.; Olivero, S. New J. Chem. 2005, 4, 633.
27. Armstrong, D. W.; Gahm, K. H.; Chang, L. W. Microchem. J. 1997, 57, 149.
28. Izumi, T.; Murakami, S. J. Chem. Technol. Biotechnol. 1994, 60, 23.
29. Miura, M.; Yoshida, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans. 1 1982, 1, 79.
30. Yadav, J. S.; Subba Reddy, V. B.; Srihari, P. Synlett 2001, 673.
31. Watahiki, T.; Akabane, Y.; Mori, S.; Oriyama, T. Org. Lett. 2003, 5, 3045.
32. Hosomi, A.; Masahiko, E.; Sakurai, H. Chem. Lett. 1976, 941.
33. Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822.