Reactions potentially related to coenzyme B12 dependent rearrangements: Observations on the radical [1,2]-acyl and -thiol ester migrations

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1986, Pages 1139-1143

  Best, Wayne M ^a   Cook, Anthony P F ^a   Russell, James J ^a   Widdowson, David A ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049067636     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19860001139     Document Type: Article

References (30)

1. 12J ed. D. Dolphin, Wiley Inter-science, New York, 1982. J. Retey, in ref. 1, vol 2, p. 357
2. R. H. Abeles, Enzyme, 1971, 5, 481
3. B. T. Golding, J. Retey, vol 1, p. 543
4. J. H. Grate, J. W. Grate, and G. N. Schrauzer, J. Am. Chem. Soc, 1982, 104, 1588
5. J. Retey and D. Arigoni, Experientia, 1966, 22, 783
6. G. J. Cardinale and R. H. Abeles, Biochem. Biophys. Acta, 1967, 132, 517
7. U. Aeberhard, R. Keese, E. Stamm, U. R. Vogeli, W. Lau, and J. K. Kochi, Helv. Chim. Acta, 1983, 66, 2740, and references there cited
8. S. Wollowitz and J. Halpern, J. Am. Chem. Soc, 1984, 106, 8319
9. A. I. Scott, J. B. Hansen, and S-K. Chung, J. Chem. Soc, Chem. Commun., 1980, 388
10. P. Dowd and M. Shapiro, Tetrahedron, 1984, 40, 3063
11. M. Tada, K. Miura, M. Okabe, S. Seki, and H. Mizukami, Chem. Lett., 1981, 33
12. M. Okabe, T. Osawa, and M. Tada, Tetrahedron Lett., 1981,22,1899
13. M. Tada, S. Akinoga, and M. Okabe, Bull. Chem. Soc. Jpn., 1982, 55, 3939
14. D. A. Lindsay, J. Lusztyk, and K. U. Ingold, J. Am. Chem. Soc, 1984, 106, 7087
15. J. J. Russell, H. S. Rzepa, and D. A. Widdowson, J. Chem. Soc, Chem. Commun., 1983, 625
16. D. G. H. Livermore and D. A. Widdowson, J. Chem. Soc, Perk in Trans. 1, 1982, 1019
17. cf. R. C. Parish and L. M. Stock, J. Org. Chem., 1965, 30, 927
18. H-J. Liu and S. I. Sabesan, Can. J. Chem., 1980, 58, 2645
19. F. W. Wenzel and E. E. Reed, J. Am. Chem. Soc, 1937,59,1089
20. J. Wemple, Tetrahedron Lett., 1975, 3255
21. A. A. Schleppnik and F. B. Zienty, J. Org. Chem., 1964, 29, 1910.
22. Ethyl 2-methyl-4-oxo-4-phenylbutyrate: N. L. Drake and W. B. Tuemmler, J. Am. Chem. Soc, 1955, 77, 1209
23. Ethyl 2-methyl-4- oxopentanoate: R. Scarpati, G. Scherillo, F. Imperato, and R. A. Nicolaus, Gazz. Chun. Itai, 1967, 97, 654
24. J. Cooper, A. Hudson, and R. A. Jackson, J. Chem. Soc, Perkin Trans. 2, 1973, 1056
25. H. G. Kuivila and C. H. Pian, J. Chem. Soc, Chem. Commun., 1974, 369
26. Y. A. Bashakov and N. G. Rozhkova, Zh. Org. Khim., 1966, 2 (8), 1423
27. Y. A. Bashakov and N. G. Rozhkova Chem. Abstr., 1967, 66, 551910
28. H. B. Kagan and Y-H. Suen, Bull. Soc. Chim. Fr., 1966, 1819
29. K. V. Auwers and M. Schmidt, Ber., 1913, 46, 494
30. W. G. Kofron and L. G. Wideman, J. Org. Chem., 1972, 37, 555