Mechanisms of Mn(OAc)3-based oxidative free-radical additions and cyclizations

Tetrahedron

Volumn 65, Issue 52, 2009, Pages 10738-10744

  Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALKENE DERIVATIVE; FREE RADICAL; MANGANESE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 70449725405     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.025     Document Type: Article

References (65)

1. Heiba E.I., Dessau R.M., and Koehl Jr. W.J. J. Am. Chem. Soc. 90 (1968) 5905
2. Bush Jr. J.B., and Finkbeiner H. J. Am. Chem. Soc. 90 (1968) 5903
3. Heiba E.I., Desaau R.M., and Rodewald P.G. J. Am. Chem. Soc. 97 (1975) 7977
4. de Klein W.J. In: Mijs W.J., and de Jonge C.R.H. (Eds). Organic Synthesis by Oxidation with Metal Compounds (1986), Plenum, New York, NY 261-314
5. Badanyan Sh.O., Melikyan G.G., and Mkrtchyan D.A. Russ. Chem. Rev. 58 (1989) 286
6. Uspekhi Khim. 58 (1989) 475
7. Melikyan G.G. Synthesis (1993) 833
8. Iqbal J., Bhatia B., and Nayyar N.K. Chem. Rev. 94 (1994) 519
9. Snider B.B. Chem. Rev. 96 (1996) 339
10. Melikyan G.G. Org. React. 49 (1997) 427
11. Melikyan G.G. Aldrichimica Acta 31 (1998) 50
12. Demir A.S., and Emrullahoglu M. Curr. Org. Syn. 4 (2007) 321
13. Fristad W.E., and Peterson J.R. J. Org. Chem. 50 (1985) 10
14. Fristad W.E., Peterson J.R., and Ernst A.B. J. Org. Chem. 50 (1985) 3143
15. Fristad W.E., Peterson J.R., Ernst A.B., and Urbi G.B. Tetrahedron 42 (1986) 3429
16. Snider B.B., Patricia J.J., and Kates S.A. J. Org. Chem. 53 (1988) 2137
17. Curran D.P., Morgan T.M., Schwartz C.E., Snider B.B., and Dombroski M.A. J. Am. Chem. Soc. 113 (1991) 6607
18. Corey E.J., and Kang M.-C. J. Am. Chem. Soc. 106 (1984) 5384
19. Kern J.M., and Federlin P. Tetrahedron Lett. (1977) 837
20. Kern J.M., and Federlin P. Tetrahedron 34 (1978) 661
21. Snider B.B., and O'Neil S. Tetrahedron 51 (1995) 12983
22. Citterio A., Fancelli D., Finzi C., Pesce L., and Santi R. J. Org. Chem. 54 (1989) 2713
23. Snider B.B., Merritt J.E., Domboski M.A., and Buckman B.O. J. Org. Chem. 56 (1991) 5544
24. Snider B.B., and McCarthy B.A. J. Org. Chem. 58 (1993) 6217
25. Snider B.B., and Smith R.B. Tetrahedron 58 (2002) 25
26. Bausch M.J., Guadalupe-Fasano C., Gostowski R., Selmarten D., and Vaughn A. J. Org. Chem. 56 (1991) 5640
27. Dunlap N.K., Sabol M.R., and Watt D.S. Tetrahedron Lett. 25 (1984) 5839
28. Demir A.S., and Jeganathan A. Synthesis (1992) 235
29. Demir A.S., Reis O., and Igdir A.C. Tetrahedron 60 (2004) 3427
30. Snider B.B., and Kiselgof E.Y. Tetrahedron 52 (1996) 6073
31. Snider B.B., Han L., and Xie C. J. Org. Chem. 62 (1997) 6978
32. Snider B.B., and McCarthy Cole B. J. Org. Chem. 60 (1995) 5376
33. McCarthy Cole B., Han L., and Snider B.B. J. Org. Chem. 61 (1996) 7832
34. Narasaka K., Miyoshi N., Iwakura K., and Okauchi T. Chem. Lett. (1989) 2169
35. Narasaka K. Pure Appl. Chem. 69 (1997) 601
36. Iwasawa N., Funahashi M., Hayakawa S., Ikeno T., and Narasaka K. Bull. Chem. Soc. Jpn. 72 (1999) 85
37. Nair V., and Deepthi A. Chem. Rev. 107 (2007) 1862
38. Baciocchi E., and Ruzziconi R. J. Org. Chem. 56 (1991) 4772
39. Baciocchi E., Giese G., Farshchi H., and Ruzziconi R. J. Org. Chem. 55 (1990) 5688
40. The structures of the final products of this reaction have been corrected:. Nair V., Mathew J., and Nair L.G. Synth. Commun. 27 (1997) 3053 and references cited therein
41. Zhang Y., and Flowers II R.A. J. Org. Chem. 68 (2003) 4560
42. Zhang Y., Raines A.J., and Flowers II R.A. Org. Lett. 5 (2003) 2363
43. Jiao J., Zhang Y., Devery III J.J., Xu L., Deng J., and Flowers II R.A. J. Org. Chem. 72 (2007) 5486
44. Casey B.M., Eakin C.A., Jiao J., Sadasivam D.V., and Flowers II R.A. Tetrahedron 65 (2009) 10762-10768
45. Baciocchi E., Paolobelli A.B., and Ruzziconi R. Tetrahedron 48 (1992) 4617
46. Kochi J.K. In: Kochi J.K. (Ed). Free Radicals Vol. 1 (1973), Wiley, New York, NY Chapter 11
47. Kochi J.K. Acc. Chem. Res. 7 (1974) 351
48. Heiba E.I., and Dessau R.M. J. Am. Chem. Soc. 93 (1971) 524
49. Heiba E.I., and Dessau R.M. J. Am. Chem. Soc. 94 (1972) 2888
50. Jenkins C.L., and Kochi J.K. J. Am. Chem. Soc. 94 (1972) 843
51. Snider B.B., and Kwon T. J. Org. Chem. 55 (1990) 1965
52. Snider B.B., and Patricia J.J. J. Org. Chem. 54 (1989) 38
53. Vinogradov M.G., Dolinko V.I., and Nikishin G.I. Bull. Acad. Sci. USSR. Ser. Chem. (1984) 1884
54. Izv. Akad. Nauk SSSR, Ser. Khim. (1984) 2065
55. Vinogradov M.G., Dolinko V.I., and Nikishin G.I. Bull. Acad. Sci. USSR. Ser. Chem. (1984) 334
56. Izv. Akad. Nauk SSSR., Ser. Khim. (1984) 375
57. Snider B.B., and Duvall J.R. Org. Lett. 6 (2004) 1265
58. O'Neil S.V., Quickley C.A., and Snider B.B. J. Org. Chem. 62 (1997) 1970
59. Snider B.B., Mohan R.M., and Kates S.A. J. Org. Chem. 50 (1985) 3659
60. Kates S.A., Dombroski M.A., and Snider B.B. J. Org. Chem. 55 (1990) 2427
61. Oumar-Mahamat H., Moustrou C., Surzur J.-M., and Bertrand M.P. J. Org. Chem. 54 (1989) 5684
62. Dale J., and Morgenlie S. Acta Chem. Scand. 24 (1970) 2408
63. Snider B.B., and McCarthy B.A. Tetrahedron 49 (1993) 9447
64. Corey E.J., and Gross A.W. Tetrahedron Lett. 26 (1985) 4291
65. Fujimoto N., Nishino H., and Kurosawa K. Bull. Chem. Soc. Jpn. 59 (1986) 3161