In grignard reagent formation from cyclopropyl bromide in diethyl ether, trapping by DCPH is consistent with diffusing cyclopropyl radical intermediates

Organic Letters

Volumn 3, Issue 4, 2001, Pages 605-606

  Garst, John F ^a   Ungváry, Ferenc ^a,b  

^a UNIVERSITY OF GEORGIA   (United States)

^b UNIVERSITY OF PANNONIA   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; ETHER DERIVATIVE; FREE RADICAL; PHOSPHINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; CYCLOPROPANES; ETHYL ETHERS; FREE RADICALS; PHOSPHINES; SOLVENTS;

EID: 0035932064     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007006d     Document Type: Article

References (24)

1. Kharasch, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Prentice Hall: New York, 1954.
2. Hamdouchi, C.; Walborsky, H. M. In Handbook of Grignard Reagents; Silverman, G. S. Rakita, P. E., Eds.; Dekker: New York, 1996; pp 145-218.
3. Garst, J. F.; Ungváry, F. In Mechanisms of Grignard Reagent Formation; Richey, H. G., Jr., Ed.; Wiley: Chichester, 2000; pp 185-275.
4. Walborsky, H. M.; Aronoff, M. S. J. Organomet. Chem. 1973, 51, 31-53.
5. Garst, J. F.; Swift, B. L.; Smith, D. W. J. Am. Chem. Soc. 1989, 111, 234-241.
6. Garst, J. F.; Deutch, J. E.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 2490-2491.
7. Garst, J. F.; Swift, B. L. J. Am. Chem. Soc. 1989, 111, 241-250.
8. Garst, J. F.; Ungvary, F.; Batlaw, R. J. Am. Chem. Soc. 1991, 113, 5392-5397.
9. Lawrence, L. M.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 2493-2494.
10. Root, K. S.; Hill, C. L.; Lawrence, L. M.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 5405-5412.
11. Ashby, E. C.; Oswald, J. J. Org. Chem. 1988, 53, 6068-6076.
12. Garst, J. F.; Ungvary, F.; Baxter, J. T. J. Am. Chem. Soc. 1997, 119, 253-254.
13. Walborsky, H. M.; Zimmermann, C. J. Am. Chem. Soc. 1992, 114, 4996-5000.
14. Péralez, E.; Négrel, J.-C.; Chanon, M. Tetrahedron Lett. 1994, 35, 5857-5860.
15. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165-168.
16. Garst, J. F.; Lawrence, K. E.; Batlaw, R.; Boone, J. R.; Ungváry, F. Inorg. Chim. Acta 1994, 222, 365-375.
17. Garst, J. F.; Ungváry, F. Unpublished results.
18. Garst, J. F.; Boone, J. R.; Webb, L.; Lawrence, K. E.; Baxter, J. T.; Ungváry, F. Inorg. Chim. Acta 1999, 296, 52-66.
19. Bodineau, N.; Mattalia, J.-M.; Thimokhin, V.; Handoo, K.; Négrel, J.-C.; Chanon, M. Org. Lett. 2000, 2, 2303-2306.
20. Markies, P. R.; Akkerman, O. S.; Bickelhaupt, F.; Smeets, W. J. J.; Spek, A. L. J. Am. Chem. Soc. 1988, 110, 4284-4292.
21. De Boer, H. J. R.; Akkerman, O. S.; Bickelhaupt, F. Angew. Chem. 1988, 100, 735-737.
22. Denney, D. B.; Denney, D. Z. Tetrahedron 1991, 47, 6577-6600.
23. Bunnett, J. F. Tetrahedron 1993, 49, 4477-4484.
24. Symons, M. C. R. Acta Chem. Scand. 1997, 51, 127-134.