Low and high temperature bromination of 2,3-dicarbomethoxy and 2,3-dicyano benzobarrelene: Unexpected substituent effect on bromination

New Journal of Chemistry

Volumn 34, Issue 1, 2010, Pages 141-150

  Takesenlioǧlu, Sara ^a   Daştan, Arif ^a   Dalkiliç, Erdin ^a   Güney, Murat ^a   Abbasoǧlu, Rza ^b  

^a ATATÜRK UNIVERSITY   (Turkey)

^b KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINE;

ARTICLE; BROMINATION; COLUMN CHROMATOGRAPHY; ELECTROPHILICITY; HIGH TEMPERATURE; INFRARED SPECTROSCOPY; LOW TEMPERATURE; MELTING POINT; PRIORITY JOURNAL; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 77956328391     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b9nj00372j     Document Type: Article

References (34)

1. D. Lenoir C. Chiappe Chem.-Eur. J. 2003 9 1036 1044
2. R. Rathore S. V. Lindeman C.-J. Zhu T. Mori P. V. R. Schleyer J. K. Kochi J. Org. Chem. 2002 67 5106 5116
3. R. S. Brown Acc. Chem. Res. 1997 30 131 137
4. P. B. D. De La Mare and R. Bolton, Electrophilic Additions to Unsaturated Systems, Elsewier, New York, 2nd edn, 1982, pp. 136-197
5. M.-F. Ruasse Adv. Phys. Org. Chem. 1993 28 207 291
6. H. Slebocka-Tilk R. G. Ball R. S. Brown J. Am. Chem. Soc. 1985 107 4504 4508
7. M. Balci A. Dastan Jr J. Chem. 2006 1 25 38
8. A. Dastan M. Balci T. Hökelek D. Ülkü O. Büyükgüngör Tetrahedron 1994 50 10555 10578
9. V. A. Barkhash Top. Curr. Chem. 1984 116-117 1 265
10. A. Dastan J. Chem. Res. (S) 2001 000 463 464
11. A. Dastan Turk. J. Chem. 2002 26 535 546
12. M. Balci O. Cakmak T. Hökelek J. Org. Chem. 1992 57 6640 6643
13. A. Dastan M. Balci Tetrahedron 2005 61 5481 5488
14. A. Dastan E. Uzundumlu M. Balci Helv. Chim. Acta 2002 85 2729 2739
15. M. E. Sengul D. D. Demirci S. Essiz E. Sahin A. Dastan Tetrahedron 2009 65 4859 4865
16. C. O. Bender D. W. Brooks Can. J. Chem. 1975 53 1684 1689
17. R. Altundas M. Balci Aust. J. Chem. 1997 50 787 793
18. A. Datan Tetrahedron 2001 57 8725 8732
19. P. Hohenberg W. Kohn Phys. Rev. 1964 136 B864 B871
20. W. Khon L. Sham Phys. Rev. 1965 140 A1133 A1138
21. C. Lee W. Yang R. G. Parr Phys. Rev. B: Condens. Matter 1988 37 785 789
22. A. D. Becke J. Chem. Phys. 1993 98 5648 5652
23. R. Krishnan J. S. Binkley R. Seeger J. A. Pople J. Chem. Phys. 1980 72 650 654
24. V. Barone M. Cossi J. Chem. Phys. 1998 102 1995 2001
25. J. Tomasi B. Mennucci R. Cami J. Chem. Phys. 2005 105 2999 3093
26. Y. Takano K. N. Houk J. Chem. Theory Comput. 2005 1 70 77
27. F. G. Bordwell T. Y. Lynch J. Am. Chem. Soc. 1989 111 7558 7562
28. S. N. Ünaldi M. Balci Tetrahedron Lett. 2001 42 8365 8367
29. R. Altundas A. Datan S. N. Ünaldi K. Güven O. Uzun M. Balci Eur. J. Org. Chem. 2002 526 533
30. T. P. Lobanova B. G. Derendyaev M. I. Kollegova V. A. Barkhash Zh. Org. Khim. (Eng. Translation) 1973 9 1883 1892
31. T. P. Lobanova N. M. Slyn'ko B. G. Derendyaev V. A. Barkhash Zh. Org. Khim., (Eng. Translation) 1973 9 1893 1900
32. L. A. Paquette W. E. Volz J. Am. Chem. Soc. 1976 98 2910 2917
33. M. Karplus J. Am. Chem. Soc. 1963 85 2870 2871
34. S. Winstein J. Am. Chem. Soc. 1961 83 1516 1517