Stepwise α-bromination of 1,1-dihaloalkenes

Synthesis

Volumn , Issue 1, 2000, Pages 139-143

  Ma, Shengming ^a   Xu, Bin ^a   Zhao, Shimin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allylic bromide; Gem dihaloalkenes; Halides; N bromosuccinimide; Radical reactions; Stepwise bromination; Wohl Ziegler reaction

Indexed keywords

BENZOYL PEROXIDE; HALOOLEFIN; N BROMOSUCCINIMIDE;

ARTICLE; BROMINATION; CATALYSIS; REACTION ANALYSIS;

EID: 0033979287     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6218     Document Type: Article

References (16)

1. (a) Wohl, A. Ber. Dtsch. Chem. Ges. 1919, 52, 5163.
2. (b) Ziegler, K.; Spath, A.; Schaaf, E.; Schumann, W.; Winkelmann, E. Liebigs Ann. Chem. 1942, 551, 80.
3. Dauben, H. J. Jr; McCoy, L. L. J. Am. Chem. Soc. 1959, 81, 4863.
4. Pizey, J. S. In Synthetic Reagents Vol, II; Wiley: New York 1974, pp 1-63.
5. Ma, S.; Xu, B. J. Org. Chem. 1998, 63, 9156.
6. Corey, E. J.; Fuchs, P. L. Tetrehedron Lett. 1972, 3769.
7. Savignac, P.; Coutrot, P. Synthesis 1976, 197.
8. (a) Rayner, C. M.; Astles, P. C.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 3926.
9. (b) Paquette, L. A.; Rayner, C. M.; Doherty, A. M. J. Am. Chem. Soc. 1990, 112, 4078.
10. Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc. Perkin Trans. 1 1991, 2575.
11. Rule, M.; Mondo, J. A.; Berson, J. A. J. Am. Chem. Soc. 1982, 104, 2209.
12. (a) Appel, R. Angew. Chem. 1975, 87, 863; Angew. Chem. Int. Ed. Engl. 1975, 14, 801.
13. (a) Appel, R. Angew. Chem. 1975, 87, 863; Angew. Chem. Int. Ed. Engl. 1975, 14, 801.
14. (b) Seyferth, D.; Marmor, R. S. J. Organomet. Chem. 1973, 59, 237.
15. Posner, G. H.; Loomis, G. L.; Sawaya, H. S. Tetrehedron Lett. 1975, 1373.
16. We have carried out this procedure many times without incident. However, as a potentially explosive compound, BPO should be stored and handled with care, see: Sax, N. I. Dangerous Properties of Industrial Materials; 6th Ed.; van Nostrand Reinhold Company Inc.: New York, 1984, p 396.