Novel radical reaction of phenylsulfonyl oxime ethers. A free radical acylation approach

Journal of the American Chemical Society

Volumn 118, Issue 21, 1996, Pages 5138-5139

  Kim, Sunggak ^a   Lee, Ill Young ^a   Yoon, Joo Yong ^a   Oh, Dong Hyun ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

CARBONYL GROUPS; FREE RADICALS; PHENYLSULFONYL OXIME ETHERS; RADICAL REACTIONS;

ETHERS;

OXIME; PHENYLSULFONYL OXIME ETHER; UNCLASSIFIED DRUG;

ACYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLIZATION; DRUG SYNTHESIS; OXIDATION; PREDICTION;

EID: 15844429509     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9600993     Document Type: Article

References (61)

1. (a) O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.13.
2. (b) Davis, B. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 3.6.
3. (a) Bentrude, W. G.; Darnall, K. R. J. Am. Chem. Soc. 1968, 90, 3588.
4. (b) Oyama, M. J. Org. Chem. 1965, 30, 2429.
5. (c) Minisci, F.; Galli, R.; Cecere, M.; Malatesta, V.; Caronna, T. Tetrahedron Lett. 1968, 5609.
6. Citterio, A.; Filippini, L. Synthesis 1986, 473. Homolytic C-alkylation of unactivated aldoximes such as acetaldoxime and phenylaldoxime gave ketoximes in very low yield (<20%).
7. Indirect approaches for formylation include additions of alkyl radicals to isonitriles and sulfonyl cyanides, (a) Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765.
8. (b) Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
9. (c) Fang, J.-M.; Chen, M.-Y. Tetrahedron Lett. 1987, 28, 2853.
10. (d) Barton, D. H. R.; Jaszberenyi, J. C.; Theodorakis, E. A. Tetrahedron Lett. 1991, 32, 3321.
11. (e) Leopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871.
12. (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295.
13. (b) Ryu, I.; Kusano, K.; Masumi, N.; Yamazaki, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1990, 31, 6887.
14. (c) Ryu, I.; Kusano, K.; Yamazaki, H.; Sonoda, N. J. Org. Chem. 1991, 56, 5003.
15. (d) Ryu, I.; Yamazaki, H.; Kusano, K.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558.
16. (e) Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 1187.
17. (a) Scott, A. I.; Kang, K. J. Am. Chem. Soc. 1977, 99, 1997.
18. (b) Wollowitz, S.; Halpern, J. J. Am. Chem. Soc. 1984, 106, 8319.
19. (c) Wollowitz, S.; Halpern, J. J. Am. Chem. Soc. 1988, 110, 3112.
20. (d) Dowd, P.; Wilk, B.; Wilk, B. K. J. Am. Chem. Soc. 1992, 114, 7949.
21. For selected examples on the use of thiol esters and selenol esters as precursors of acyl radicals, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv: Chim. Acta 1980, 63, 2328.
22. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377.
23. (c) Boger, D. L.; Mathvink, R. L. J. Am. Chem. Soc. 1990, 112, 4003.
24. (d) Boger, D. L.; Mathvink, R. L. J. Am. Chem. Soc. 1990, 112, 4008.
25. (e) Curran, D. P.; Liu, H. J. Org. Chem. 1991, 56, 3463.
26. (f) Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875.
27. (g) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31.
28. (h) Chatgilialoglu, C.; Lucarini, M. Tetrahedron Lett. 1995, 36, 1299.
29. Harendza, M.; Junggebauer, J.; Lebmann, K.; Neuman, W. P.; Tews, H. Synlett 1993, 286.
30. In addition to 3a, S-phenyl 4-phenoxypentanethioate (6%) was isolated along with recovery of 2a (40%).
31. (a) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc 1989 111, 230.
32. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989 111, 2614.
33. (c) Walton, R.; Fraser- Reid, B. J. Am. Chem. Soc. 1991 113, 5791.
34. (d) Beckwith, A. L. J.; Raner, K. D. J, Org. Chem. 1992, 57, 4954
35. (a) Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
36. (b) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631.
37. (c) Bartlett, P. A.; Mclaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 110, 1633.
38. (d) Parker, K. A.; Spero, D. M.; Epp, J. V. J. Org. Chem. 1988, 53, 4628.
39. (e) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727.
40. (f) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248.
41. (g) Barton, D. H. R.; Dalko, P. I.; Gero, S. D. Tetrahedron Lett. 1991, 32, 4713.
42. (h) Hatem, J.; Henriet-Bernard, C.; Grimaldi, J.; Maurin, R. Tetrahedron Lett. 1992, 33, 1057.
43. (i) Contelles, J. M.; Ruiz, P.; Sanchez, B.; Jimeno, M. L. Tetrahedron Lett. 1992, 33, 5261.
44. (j) Hart, D. J.; Krishnamurthy, R.; Pook, L. M.; Seely, F. L. Tetrahedron Lett. 1993, 34, 7819.
45. (k) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205.
46. (l) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253.
47. According to our kinetic and competition studies on the rate constant for 5- exo and 6-exo cyclization of primary alkyl radicals to the O-benzyl oxime ethers, C=N bonds in oxime ethers seem to be much better radical acceptors than C=C and C=O bonds. Kim, Y. J. Unpublished results.
48. (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882.
49. (b) Kim, S.; Kee, I. S. Tetahedron Lett. 1993, 34, 4213.
50. (c) Kim, S.; Cheong, J. H.; Yoon, K. S. Tetrahedron Lett. 1995, 36, 6069.
51. (d) Sturino C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447.
52. (e) Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514.
53. 2 in 26% yield.
54. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds: Pergamon Press: New York, 1986; Chapter 2.
55. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions: John Wiley & Sons: London, 1976; Chapter 4 and 5.
56. The preparation of 4c (mp 51-52°C) and 4d (mp 45-46°C) is as follows. (Equation Presented)
57. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1991; p 214.
58. The use of bis(tributyltin) gave similar yields in most cases. However, separation of the product from O-benzyl pentanaldoxime was difficult in several cases.
59. 1H NMR spectrum of the corresponding ketones after deprotection of O-benzyl oxime ether group.
60. Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872.
61. 3 (1.2 equiv), 4c or 4d (2.0 equiv), and acetone (5.0 equiv) in benzene (0.3 M in substrate) at 300 nm for 4 h (alkyl iodides) and for 12 h (alkyl bromides).