Alkylation of remote non-activated δ-carbon atoms: Addition of δ- carbon radicals, generated by 1,5-hydrogen transfer in alkoxy radical intermediates, to activated olefins

Tetrahedron

Volumn 55, Issue 5, 1999, Pages 1377-1390

  Petrović, Goran ^a,b   Čeković, Živorad ^a,b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENESULFENATE; FREE RADICAL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; INFRARED SPECTROMETRY; IRRADIATION; PHOTOLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033613672     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01110-7     Document Type: Article

References (54)

1. Leading references: a) Curran, D. P. in Comprehensive Organic Synthesis, Trost, B., Fleming, I.; Eds. Pergamon Press; Oxford, 1991; Vol. 4, p.715.
2. b)Giese, B. Radicals in Organic Synthesis. Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
3. c) Curran, D. P. Synthesis, 1988, 417 and 489.
4. c) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH, Weinheim, 1995.
5. d) Giese, B.; Kopping, B; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. Reactions, 1996, 48, 301 John Wiley, New York,
6. e) Barton, D. H. R.; Parekh, S. I. Half Century of Free Radical Chemistry, Cambridge University Press, 1993.
7. f) Regitz, M.; Giese, B. C-radicale, in Houben-Weil, Methoden der Organischen Chemie, Vol. E19a, Georg Thieme Verlag, Stuttgart, 1989.
8. g) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev.,1991, 91, 1237.
9. a) Heusler, K,; Kalvoda, J. Angew. Chem. Int. Ed. Engl., 1964, 3, 525.
10. b) Mihailović M. Lj.; Ceković, Z. Synthesis, 1970, 209.
11. c) Kalvoda, J.; Heusler, K. Synthesis, 1971, 501.
12. d) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076.
13. e) Majetich, G.; Wheless, K. Tetrahedron, (Rep. No. 375), 1995, 51, 7095.
14. f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207.
15. g) Wolf, M. E. Chem. Rev. 1963, 63, 55.
16. a) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601.
17. b) Barton, D. H. R. Pure and Appl. Chem. 1968, 16, 1.
18. c) Hesse, R. H. Advan. in Free Radical Chem. 1969, 3, 83.
19. a) Mihailović, M. Lj.; Čeković, Ž.; Lorenc, Lj. Organic Synthesis by Oxidationwith Metal Compounds, Mijs, W. J.; de Jonge, C. R. H. I., Eds. Plenum Press, New York, 1986, p. 758.
20. b) Mihailović, M. Lj.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, Lj.; Mamuzić, R. I. Tetrahedron, 1965, 21, 2799.
21. c) Mihailović M. Lj.; Čeković, Ž. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed., Vol. V. p. 2949, John Wiley, Chichester, 1995.
22. a) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597.
23. b) Mihailović, M. Lj.; Čeković, Ž,; Stanković, J. J. Chem. Soc., Chem. Commun. 1969, 981.
24. c) Čeković Ž,; Green, M. M. J. Am. Chem. Soc. 1974, 96, 3000.
25. d) Čeković, Ž.; Dimitrijević, Lj.; Djokić, G.; Srnić, T. Tetrahedron, 1979,35; 2021.
26. a) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657.
27. b) Van de Woude, G.; van Hove, L. Bull. Soc. Chim. Belg. 1973, 82, 49; 1975, 84, 911.
28. b) Van de Woude, G.; van Hove, L. Bull. Soc. Chim. Belg. 1973, 82, 49; 1975, 84, 911.
29. a) Curran, D. P.; Shen, W. J. J. Am. Chem. Soc. 1993, 115, 6051.
30. b) Breslow, R. Chem. Soc. Rev. 1972, 1, 553.
31. c) Breslow, R.; Snider, B. B.; Corcoran, R. J. J. Am. Chem. Soc. 1974, 96, 6792.
32. a) Dorigo, A. E.; Houk, K. N. J. Org. Chem. 1988, 53, 1650.
33. b) Green, M. M.; Boyle, B. A.; Vairamani, M.; Mukhopadhyay, T.; Saunders, W. H.; Bowen, P.; Allinger N. L. J. Am/. Chem. Soc. 1986, 108, 2381.
34. c) Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Acc. Chem. Res. 1990, 23, 107.
35. d) Nedelec, J. Y.; Grunselle, M.; Triki, A.; Lefort, D. Tetrahedron, 1977, 33, 39.
36. a) Gilbert, B. C.; Holmes, R. G. G.; Lane, H. A. H.; Norman, R. O. C. J. Chem. Soc., Perkin II, 1976, 1047.
37. b) Beckwith, A. L. J. Ingold, K. U. Free Radical Rearrangements, in Rearrangements in Ground and Excited States, de Mayo, P. Ed. Acadamic Press, New York, 1980, 1, 161.
38. a) Čeković Ž.; Cvetković M. Tetrahedron Lett. 1982, 23, 3791.
39. b) Čeković, Ž. Rad Jugosl. Akad. Znan. i Umjet, Kem. 1983, 2, 21.
40. Čeković, Ž,; Djokić, G. Tetrahedron, 1981, 37, 4263.
41. Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561.
42. Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441.
43. Riemann, H,; Capomaggi, A. S.; Strauss, T.; Oliveto, E. P.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 4481.
44. Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356.
45. Tsunoi, S.; Ryu, I.: Sonoda, N. J. Am. Chem. Soc. 1994, 116, 5473.
46. a) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627
47. b) Petrović, G.; Saičić, R. N.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 7107.
48. Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143.
49. Beckwith, A. L. J.; Hay, B. P. Williams, G. M. J. Chem. Soc., Chem. Commun. 1989,1202
50. a) Hartung, J.; Gallon, F.J. Org. Chem. 1995, 60, 6706.
51. b) Guindon, Y.: Denis, R. C. Tetrahedron Lett. 1998, 39, 339.
52. Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051.
53. Hunter, C. J. Chem. Soc. 1936, 285.
54. Barrett, A. G. M.; Dhanak. D.; Graboski, G. G.; Taylor, S. J. Org. Synthesis, Coll. Vol. VIII, 550, Freeman, J. P. Ed. John Wiley, New York, 1993.