Free radical chemistry of lactones: Ring contractions and expansions

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7422-7423

  Crich, David ^a   Beckwith, Athelstan L J ^b   Filzen, G Fredrick ^a   Longmore, Robert W ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029759834     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960471e     Document Type: Article

References (46)

1. (a) Surzur, J.-M.; Teisser, P. C.R. Seances Acad. Sci., Ser. C 1967, 264, 1981.
2. (b) Surzur, J.-M.; Teisser, P. Bull. Soc. Chim. Fr. 1970, 3060.
3. (c) Tanner, D. D.; Law, F. C. J. Am. Chem. Soc. 1969, 91, 7537.
4. (a) Beckwith, A. L. J.; Tindal, P. L. Aust. J. Chem. 1971, 24, 2099.
5. (b) Perkins, M. J.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1975, 77.
6. (c) Beckwith, A. L. J.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 2 1973, 861.
7. (d) Barclay, L. R. C.; Griller, D.; Ingold, K. U. J. Am. Chem. Soc. 1982, 104, 4399.
8. (e) Barclay, L. R. C.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 1793.
9. (f) Saebo, S.; Beckwith, A. L. J.; Radom, L. J. Am. Chem. Soc. 1984, 104, 5119.
10. (g) Julia, S.; Lome, R. C.R. Acad. Seances Sci., Ser. C 1971, 273, 174.
11. (h) Julia, S.; Lorne, R. Tetrahedron 1986, 42, 5011.
12. (h) Giese, B.; Gilges, S.; Groninger, K. S.; Lamberth, C.; Witzel, T. Liebigs Ann. Chem. 1988, 615.
13. (i) Giese, B.; Groninger, K. S. Org. Synth. 1990, 69, 66.
14. (j) Evanochko, W. T.; Shevlin, P. B. J. Org. Chem. 1979, 44, 4426.
15. (k) Kocovsky, P.; Stary, I.; Turecek, F. Tetrahedron Lett. 1986, 27, 1513.
16. (l) Beckwith, A. L. J.; Duggan, P. J. J. Chem. Soc., Perkin Trans. 2 1992, 1777.
17. (m) Korth, H.-G.; Sustmann, R.; Groninger, K. S.; Leisung, M.; Giese, B. J. Org. Chem. 1988, 53, 4364.
18. (n) Beckwith, A. L. J.; Duggan, P. J. J. Chem. Soc., Perkin Trans. 2 1993, 1673.
19. (a) Crich, D.; Jiao, X.-Y. J. Am. Chem. Soc. 1996, 118, 0000.
20. (b) Crich, D.; Yao, Q.; Filzen, G. F. J. Am. Chem. Soc. 1995, 117, 11455.
21. (c) Crich, D.; Yao, Q. J. Am. Chem. Soc. 1994, 116, 2631.
22. (d) Crich, D.; Yao, Q. Tetrahedron Lett. 1993, 34, 5677.
23. (e) Crich, D.; Yao, Q. J. Am. Chem. Soc. 1993, 115, 1165.
24. (f) Koch, A.; Giese, B. Helv. Chim. Acta 1993, 76, 1687.
25. (g) Koch, A.; Lamberth, C.; Wettrich, F.; Giese, B. J. Org. Chem. 1993, 58, 1083.
26. (a) Crich, D.; Filzen, G. F. Tetrahedron Lett. 1993, 34, 3225.
27. (b) Crich, D.; Filzen, G. F. J. Org. Chem. 1995, 60, 4834.
28. (a) Sprecher, M. Chemtracts: Org. Chem. 1994, 7, 115.
29. (b) For fragmentations of β-(phosphatoxy)alkyl radicals, see: Giese, B.; Beyrich-Graf, X.; Burger, J.; Kesselheim, C.; Senn, M.; Schäfer, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1742.
30. (a) Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171.
31. (b) Nicolaou, K. C. Tetrahedron 1981, 37, 4097.
32. Furber, M.; Kraft-Klaunzer, P.; Mander, L. N.; Pour, M.; Yamaguchi, T.; Murofushi, N.; Yamane, H.; Schraudolf, H. Aust. J. Chem. 1995, 48, 427.
33. (a) Inanaga, J.; Hirata, K.; Saiki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
34. (b) Review on medium ring lactone chemistry: Rousseau, G. Tetrahedron 1995, 51, 2777.
35. We recognize that for experiments conducted with syringe pump additions the stationary concentrations of stannane may not be totally reproducible from experiment to experiment and so hestitate to derive precise relative rates from the data in Table 1.
36. (a) Huisgen, R.; Ott, H. Tetrahedron 1959, 6, 253.
37. (b) Clossen, W.; Orenski, P. J. Org. Chem. 1967, 32, 3160.
38. (c) Kaiser, E.; Kezdy, F. Prog. Bioorg. Chem. 1976, 4, 239.
39. (a) Schweizer, W. B.; Dunitz, J. D, Helv. Chim. Acta 1982, 65, 1547.
40. (b) Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Saunders, M. J. Am. Chem. Soc. 1991, 113, 971.
41. -1): 5/8.8 ± 0.9; 6/11.2 ± 0.9; 7/10.7 ± 0.7; 8/12.4 ±0.8; 9/11.6 ± 0.8; 10/8.2 ± 0.8; 11/7.3 ± 0.7; 12/7.1 ± 0.9; 13/6.7 ± 0.8; 14/4.5 ± 0.8.
42. (a) Chen, K. S.; Kochi, J. K. J. Am. Chem. Soc. 1974, 96, 1383.
43. (b) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143.
44. The cis geometry of 36 was confirmed by nOe difference spectrocopy.
45. (a) Crich, D.; Yao, Q. J. Org. Chem. 1995, 60, 84.
46. (b) Crich, D.; Crich, D.; Hwang, J.-T.; Liu, H. Tetrahedron Lett. 1996, 37, 3105.