Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds

Tetrahedron Letters

Volumn 50, Issue 6, 2009, Pages 700-703

  Tatar, Jovana ^a   Baranac Stojanović, Marija ^a,b   Stojanović, Milovan ^a   Marković, Rade ^a,b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; NUCLEOPHILE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON TRANSPORT; SUBSTITUTION REACTION;

EID: 57749201586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.104     Document Type: Article

References (36)

1. Zefirov N.S., and Makhon'kov D.I. Chem. Rev. 82 (1982) 615-624
2. Braverman S., Pechenick-Azizi T., Major D.T., and Sprecher M. J. Org. Chem. 72 (2007) 6824-6831
3. Sazonov P.K., Artamkina G.A., Khrustalev V.N., Antipin M.Yu., and Beletskaya I.P. J. Organomet. Chem. 681 (2003) 59-69
4. Saito M., Okuyama Y., Tajima T., Kato D., and Yoshioka M. Appl. Organomet. Chem. 21 (2007) 604-611
5. Galli C., and Rappoport Z. Acc. Chem. Res. 36 (2003) 580-587
6. Moser D.F., Bosse T., Olson J., Moser J.L., Guzei I.A., and West R. J. Am. Chem. Soc. 124 (2002) 4186-4187
7. Li X.-Y., Pan H.-Q., and Jiang X. Tetrahedron Lett. 25 (1984) 4937-4940
8. Li X.-Y., Pan H.-Q., and Jiang X.-K. Tetrahedron Lett. 28 (1987) 3699-3702
9. Cox D.G., and Burton D.J. J. Org. Chem. 53 (1988) 366-374
10. Wakselman C., and Tordeux M. J. Org. Chem. 50 (1985) 4047-4051
11. Gentile A.M., and Mencarelli P. Gazz. Chim. Ital. 118 (1988) 609-610
12. Baciocchi E., and Lillocci C. J. Chem. Soc., Perkin Trans. 2 (1973) 38-41
13. Yasui S., Itoh K., and Ohno A. Heteroat. Chem. 12 (2001) 217-222
14. Dahl O. J. Chem. Soc., Perkin Trans. 1 (1978) 947-954
15. Fishwick B.R., Rowles D.K., and Stirling C.J.M. J. Chem. Soc., Perkin Trans. 1 (1986) 1171-1179
16. Grinblat J., Ben-Zion M., and Hoz S. J. Am. Chem. Soc. 123 (2001) 10738-10739
17. Grossert J.S., Dubey P.K., and Elwood T. Can. J. Chem. 63 (1983) 1263-1267
18. Galvagni M., Kelleher F., Paradisi C., and Scorrano G. J. Org. Chem. 55 (1990) 4454-4456
19. Mebane R.C., Smith K.M., Rucker D.R., and Foster M.P. Tetrahedron Lett. 40 (1999) 1459-1462
20. Shen Y., and Yang B. J. Chem. Soc., Chem. Commun. (1988) 1394-1395
21. Underwood G.R., and Dietze P.E. J. Org. Chem. 49 (1984) 5225-5229
22. Eberson L., Finkelstein M., Folkesson B., Hutchins G.A., Jönsson L., Larsson R., Moore W.M., and Ross S.D. J. Org. Chem. 51 (1986) 4400-4403
23. Baranac-Stojanović M., Tatar J., Kleinpeter E., and Marković R. Synthesis (2008) 2117-2121
24. Marković R., Džambaski Z., and Baranac M. Tetrahedron 57 (2001) 5833-5841
25. For selective mono- and dibromination of o-hydroxy- and o-methoxyacetophenones, see:. Juneja S.K., Choudhary D., Paul S., and Gupta R. Synth. Commun. (2006) 2877-2881
26. King L.C., and Ostrum G.K. J. Org. Chem. 29 (1964) 3459-3461
27. Arbuj S.S., Waghmode S.B., and Ramaswamy A.V. Tetrahedron Lett. 48 (2007) 1411-1415
28. Pravst I., Zupan M., and Stavber S. Tetrahedron 64 (2008) 5191-5199
29. For selective dibromination of meta- and para-substituted acetophenones, see:. Kajigaeshi S., Kakinami T., Tokiyama H., Hirakawa T., and Okamoto T. Bull. Chem. Soc. Jpn. 60 (1987) 2667-2668
30. Paul S., Gupta V., Gupta R., and Loupy A. Tetrahedron Lett. 44 (2003) 439-442
31. Diwu Z., Beachdel C., and Kalubert D.H. Tetrahedron Lett. 39 (1998) 4987-4990
32. 2: C, 35.10; H, 2.62. Found: C, 35.32; H, 2.78.
33. Yadav J.S., Subba Reddy B.V., Subba Reddy U.V., and Chary D.N. Synthesis (2008) 1283-1287
34. Malaitong N., and Thebtaranonth C. Chem. Lett. (1980) 305-306
35. 2O, drying, and evaporation, the crude products 10a-g were purified by column chromatography on silica gel, using petroleum ether/ethyl acetate gradient 100:0 to 80:20 (v/v).
36. At the present time it is not possible to rule out that the bromophilic step precedes the carbophilic step.