An investigation of the reactivity of MCPBA and α-bromoalkenes under traditional or microwave-assisted conditions: Selective formation of epoxides or allylic bromides

Synlett

Volumn , Issue 14, 2005, Pages 2204-2208

  Benfatti, Fides ^a   Cardillo, Giuliana ^a   Gentilucci, Luca ^a   Perciaccante, Rossana ^a   Tolomelli, Alessandra ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

bromo derivatives; Epoxidation; Microwaves; Radical reactions; Rearrangements

Indexed keywords

3 CHLOROPERBENZOIC ACID; ALKENE DERIVATIVE; BROMIDE; BROMINE DERIVATIVE; EPOXIDE; ESTER; LACTAM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DILUTION; MICROWAVE RADIATION; REACTION ANALYSIS;

EID: 24744449297     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872254     Document Type: Article

References (36)

1. For general accounts on MCPBA reactions, see: (a) Comprehensive Organic Synthesis, Vol. 7; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 357-372.
2. (b) Paquette, L. Encyclopedia of Reagents for Organic Synthesis, Vol. 2; John Wiley and Sons: New York, 1995, 1192-1198.
3. Prilezhaev, N. Ber. 1909, 42, 4811.
4. For the well-known 'butterfly' mechanism of epoxidation see: (a) Bartlett, P. A. Rec. Chem. Prog. 1957, 18, 111.
5. For some recent reports on the radical hypothesis see: (b) Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616.
6. (c) Okovytyy, S.; Gorb, L.; Leszczynski, J. Tetrahedron 2002, 58, 8751.
7. (d) Bach, R. D.; Glukhovtsev, M. N.; Gonzalez, C. J. Am. Chem. Soc. 1998, 120, 9902.
8. (a) Warrener, R. N.; Elsey, G. M.; Pitt, I. G.; Russell, R. A. Aust. J. Chem. 1995, 48, 241.
9. For the synthesis of α-haloepoxides see also: (b) Ono, T.; Henderson, P. Tetrahedron Lett. 2002, 43, 7961.
10. (c) Taber, D. F.; Mitten, J. V. J. Org. Chem. 2002, 67, 3847.
11. (d) Benayoud, F.; Begue, J. P.; Bonnet-Delpon, D.; Fischer-Durand, N.; Sdassi, H. Synthesis 1993, 1083.
12. Kocienski, P. J. Chem. Soc., Perkin Trans, 1 1983, 945.
13. Nakayama, J.; Kamiyama, H. Tetrahedron Lett. 1992, 49, 7539.
14. (a) Benfatti, F.; Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Piccinelli, F.; Tolomelli, A. Synthesis 2005, 61.
15. (b) Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Piccinelli, F.; Tolomelli, A. Org. Lett. 2005, 4, 533.
16. (c) Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Tolomelli, A. Adv. Synth. Catal. 2005, 6, 833.
17. (d) Benfatti, F.; Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Tolomelli, A. ARKIVOC 2005, (vi), 136.
18. -1.
19. (a) Alcaide, B.; Almendros, P. Curr. Med. Chem. 2004, 11, 1921.
20. (b) Deshmukh, A. R. A. S.; Bhawal, B. M.; Krishnaswamy, D.; Govande Vidyesh, V.; Shinkre Bidhan, A.; Jayanthi, A. Curr. Med. Chem. 2004, 11, 1889.
21. (c) Singh, G. S. Tetrahedron 2003, 59, 7631.
22. (d) Miller, M. J.; Hsiao, C. N.; Huang, N. Z.; Kalish, V. J.; Peterson, K.; Rajendra, G. Recent Adv. Chem. β-Lactam Antibiot. 1989, 70, 273; special publication of the Royal Society of Chemistry, London.
23. (e) Ojima, I.; Shimizu, N.; Qiu Xiaogang, C.; Hauh, J. C.; Nakahashi, K. Bull. Soc. Chim. Fr. 1987, 4, 649.
24. (a) Hayes, B. L. Aldrichimica Acta 2004, 37, 66.
25. (b) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
26. (a) Hanzlik, R. P.; Shearer, G. O. J. Am. Chem. Soc. 1975, 97, 5231.
27. (b) Kropf, H.; Yazdanbachsch, M. R. Tetrahedron 1974, 30, 3455.
28. Zhang, H. Y.; Sun, Y. M.; Wang, X. L. J. Org. Chem. 2002, 67, 2709.
29. Ogata, Y.; Tabushi, I. J. Am. Chem. Soc. 1961, 83, 3440.
30. Microwave-assisted reactions have been performed on a Milestone Microsynth Labstation, dual magnetron system with pyramid diffuser, 1600 W power (800X2), maximum delivered power 1000 W, Easywave software. Conditions: 200 W fixed power, 5 min irradiation.
31. (a) Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Tolomelli, A. Tetrahedron: Asymmetry 2004, 15, 593.
32. (b) Cardillo, G.; De Simone, A.; Mingardi, A.; Tomasini, C. Synlett 1995, 1131; and reference cited therein.
33. -1. (17) Fujita, M.; Ishizuka, H.; Ogura, K. Tetrahedron Lett. 1991, 32, 6355.
34. (a) Bonini, C.; Righi, G. Synthesis 1994, 225.
35. (b) Wang, S.; Howe, G. P.; Mahal, R. S.; Procter, G. Tetrahedron Lett. 1992, 33, 3351.
36. -1.