Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies

Tetrahedron

Volumn 65, Issue 7, 2009, Pages 1430-1437

  Ali, Mohamed Fadelalla ^a   Çalişkan, Raşit ^a,b   Şahin, Ertan ^c   Balci, Metin ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b SULEYMAN DEMIREL UNIVERSITY   (Turkey)

^c ATATÜRK UNIVERSITY   (Turkey)

Author keywords

Benzobarrelene; Cycloaddition; Free radicals; Homobenzonorbornadiene; Manganese triacetate; Rearrangement

Indexed keywords

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; ACETYLACETONE; BENZOBARRELENE; FREE RADICAL; HOMOBENZONORBORNADIENE; MANGANESE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 58149351336     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.012     Document Type: Article

References (55)

1. Bush J.B., and Finkbeiner H. J. Am. Chem. Soc. 90 (1968) 5903
2. Heiba E.I., Dessau R.M., and Koehl W.J. J. Am. Chem. Soc. 90 (1968) 5905
3. Snider B.B. Chem. Rev. 96 (1996) 339
4. Iqbal J., Bhatia B., and Nayyar N.K. Chem. Rev. 94 (1994) 519
5. Melikyan G.G. Synthesis (1993) 833
6. For general radical cyclization, see:
7. Julia M. Acc. Chem. Res. 4 (1971) 386
8. Breslow R., Olin S.S., and Groves J.T. Tetrahedron Lett. (1968) 1837
9. Snider B.B., and O'Neil S.V. J. Org. Chem. 47 (1995) 12983
10. Wang G.-W., Dong Y.-W., Wu P., Yuan T.-T., and Shen Y.-B. J. Org. Chem. 73 (2008) 7088 10.1021/jo800870z
11. Alvarez-Manzaneda E., Chahboun R., Cabrera E., Alvarez E., Alvarez-Manzaneda R., Lachkar M., and Messouri I. Synlett (2007) 2425
12. Burgaz E.V., Yilmaz M., Pekel A.T., and Oktemer A. Tetrahedron 63 (2007) 7229
13. Singh O.V., Huang W.-J., Chen C.-H., and Lee S.-S. Tetrahedron Lett. 48 (2007) 8166
14. Shing T.K.M., Yeung Y.-Y., and Su P.L. Org. Lett. 8 (2006) 3149
15. Tsai A.-I., Lin C.-H., and Chuang C.-P. Heterocycles 65 (2005) 2381
16. Chen H.-L., Lin C.-Y., Cheng Y.-C., Tsai A.-I., and Chuang C.-P. Synthesis (2005) 977
17. Huang J.-W., and Shi M. J. Org. Chem. 70 (2005) 3859
18. Nguyen V.-H., and Nishino H. Tetrahedron Lett. 45 (2004) 3373
19. Snider B.B., and Smith R.B. Tetrahedron 58 (2002) 25
20. Zhang Q., Mohan R.M., Cook L., Kazanis S., Peisach D., Foxman B.M., and Snider B.B. J. Org. Chem. 58 (1993) 7640
21. Kates S.A., Dombroski M.A., Curran D.P., Morgan T.M., Schwartz T.M., Snider B.B., and Dombroski M.A. J. Am. Chem. Soc. 113 (1991) 6607
22. Snider B.B. J. Org. Chem. 55 (1990) 2427
23. Snider B.B., Mohan R.M., and Kates S.A. J. Org. Chem. 50 (1985) 3659
24. Ernst A.B., and Fristad W.E. Tetrahedron Lett. 26 (1985) 3761
25. Corey E.J., and Kang M.-C. J. Am. Chem. Soc. 106 (1984) 5384
26. Heiba E.I., and Dessau R.M. J. Am. Chem. Soc. 93 (1971) 524
27. Heiba E.I., and Dessau R.M. J. Am. Chem. Soc. 94 (1972) 2888
28. Heiba E.I., and Dessau R.M. J. Am. Chem. Soc. 96 (1974) 7977
29. Fristad W.E., Peterson J.R., Ernst A.B., and Urbi G.B. Tetrahedron 42 (1986) 3442
30. Fristad W.E., and Peterson J.R. J. Org. Chem. 50 (1985) 10
31. Çali{dotless}şkan R., Ali M.F., Şahin E., Watson W.H., and Balci{dotless} M. J. Org. Chem. 72 (2007) 3353
32. Çali{dotless}şkan R., Pekel T., Watson W.H., and Balci M. Tetrahedron Lett. 46 (2005) 6227
33. Whitesides G.M., and San Flippo Jr. J. J. Am. Chem. Soc. 92 (1970) 6611
34. Davies D.I., and Cristol S.J. Adv. Free-Radical Chem. 1 (1965) 155
35. Senocak E., Taskesenligil Y., and Tumer F. Turk. J. Chem. 26 (2002) 939
36. Dastan A., Taskesenligil Y., and Tumer F. Tetrahedron 52 (1996) 14005
37. Dastan A., Demir U., and Balci M. J. Org. Chem. 59 (1994) 6534
38. Balci M., Cakmak O., and Hokelek T. J. Org. Chem. 57 (1992) 6640
39. Cakmak O., and Balci M. J. Org. Chem. 54 (1989) 181
40. Wilt J.W., Gutman G., Ranus Jr. W.J., and Zigman A.R. J. Org. Chem. 32 (1967) 893
41. Cristol S.J., and Nachtigall G.W. J. Org. Chem. 32 (1967) 3727
42. Johnson R.P., Exarchou A., Jefford C.W., and Hahn R.C. J. Org. Chem. 42 (1977) 3758
43. Mohan R., Kates S.A., Dombroski M., and Snider B.B. Tetrahedron Lett. 28 (1987) 845
44. Bertrand M.P., Surzur J.-M., Oumar-Mahamat H., and Moustrou C. J. Org. Chem. 56 (1991) 3089
45. Shishido K., Goto K., Tsuda A., Takaishi Y., and Shibuya M. J. Chem. Soc., Chem. Commun. (1993) 793
46. Snider B.B., Mohan R., and Kates S.A. Tetrahedron Lett. 28 (1987) 841
47. Snider B.B., and Dombroski M.A. J. Org. Chem. 52 (1987) 5487
48. Snider B.B., Merrit J.E., Dombroski M.A., and Buckman B.O. J. Org. Chem. 56 (1991) 5544
49. Oumar-Mahamat H., Moustrou C., Surzur J.-M., and Bertrand M.P. J. Org. Chem. 54 (1989) 5684
50. Tanyeli C., Ozdemirhan D., and Sezen B. Tetrahedron 58 (2002) 9983
51. Rondan N.G., Paddon-Row M.N., Caramella P., and Houk K.N. J. Am. Chem. Soc. 103 (1981) 2436
52. Ermer O., Bell P., and Mason A. Angew. Chem., Int. Ed. Engl. 28 (1989) 1239
53. Balci M., Güney M., Dastan A., and Azizoglu A. J. Org. Chem. 72 (2007) 4756
54. For similar rearrangement on benzobarrelene, see:. Dastan A., Balci M., Hokelek T., Ulku D., and Buyukgungur O. Tetrahedron 50 (1994) 10555
55. Mancera O., Rosenkranz G., and Sondheimer F. J. Chem. Soc. (1953) 2189