Ring contraction of N-chlorolactams, a novel rearrangement

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4285-4288

  Drouin, Alexandre ^a   Lessard, Jean ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

N Chlorolactams; Nitrogen heterocycles; Photolysis; Rearrangement; Ring contraction

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBON; CHLORINE DERIVATIVE; DICHLOROMETHANE; LACTAM DERIVATIVE; N CHLOROLACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PHOTOLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33747490417     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.024     Document Type: Article

References (38)

1. For review articles about chemistry of amidyls radical see:. Esker J., and Newcomb M. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 58 (1993), Academic Press, New York 1
2. Fallis A.G., and Brinza I.M. Tetrahedron 53 (1997) 17543
3. Stella L. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim, Germany 407
4. Back T.G., and Brunner K. J. Org. Chem. 54 (1989) 1904
5. Phan X.T., and Shannon P.J. J. Org. Chem. 48 (1983) 5164
6. Neale R.S., Marcus N.L., and Schepers R.G. J. Am. Chem. Soc. 88 (1966) 3051
7. Chow Y.L., and Perry R.A. Tetrahedron Lett. 13 (1972) 531
8. Kuehne M.E., and Horne D.A. J. Org. Chem. 40 (1975) 1287
9. Intramolecular radical additions:. Mackiewicz P., Furstoss R., Waegell B., Côté R., and Lessard J. J. Org. Chem. 43 (1978) 3746-3750
10. Lessard J., Côté R., Mackiewicz P., Furtoss R., and Waegell B. J. Org. Chem. 43 (1978) 3750-3756
11. Intermolecular additions:. Touchard D., and Lessard J. Tetrahedron Lett. 12 (1971) 4425
12. Touchard D., and Lessard J. Tetrahedron Lett. 14 (1973) 3827
13. Driguez H., Paton J.M., and Lessard J. Can. J. Chem. 55 (1977) 700
14. Driguez H., and Lessard J. Can. J. Chem. 55 (1977) 720
15. Driguez H., and Lessard J. Can. J. Chem. 56 (1978) 119
16. Flesia E., Croatto A., Tordo P., and Surzur J.M. Tetrahedron Lett. (1972) 535
17. Neale R.S. Synthesis (1971) 1 and references cited therein
18. Johnson R.A., and Greene F.D. J. Org. Chem. 40 (1975) 2186
19. Joseph T.C., Tam J.N.S., Kitadani M., and Chow Y.L. Can. J. Chem. 54 (1976) 3517
20. Barton D.H.R., Beckwith A.L.J., and Goosen A. J. Chem. Soc. (1965) 181
21. Beckwith A.L.J., and Goodrich J.E. Aust. J. Chem. 18 (1965) 747
22. N:. Lessard J., Griller D., and Ingold K.U. J. Am. Chem. Soc. 102 (1980) 3262-3264
23. Sutcliffe R., Griller D., Lessard J., and Ingold K.U. J. Am. Chem. Soc. 103 (1981) 624-628
24. Sutcliffe R., Ingold K.U., and Lessard J. J. Am. Chem. Soc. 103 (1981) 7685-7686
25. Daoust B., and Lessard J. Tetrahedron 55 (1999) 3495-3514
26. All N-chlorolactams were prepared from their corresponding lactams, see Supplementary data for procedure.
27. N state of an amidyl radical with an olefin has been reported in the literature to date.
28. Edwards O.E., Grue-Sorensen G., and Blackwell B.A. Can. J. Chem. 75 (1997) 857-872
29. Smith M.B., and March J. Advanced Organic Chemistry. 5th ed. (2001), Wiley Interscience 1411-1415
30. Johnson R.A., and Greene F.D. J. Org. Chem. 40 (1975) 2192-2196
31. Bloomfield G.F. J. Chem. Soc. (1944) 114
32. Adam J., Gosselain P.A., and Goldfinger P. Nature (London) 171 (1953) 704-705
33. This is well known in ionic rearrangements but no example of a radical migration of an alkyl group has been reported according to our knowledge. See:. Smith M.B., and March J. Advanced Organic Chemistry. 5th ed. (2001), Wiley Interscience 1384-1386
34. For a discussion of similar electron transfers see:. Kropp P.J. Acc. Chem. Res. 17 (1984) 131
35. Ho P.-T. Can. J. Chem. 56 (1979) 733
36. Zimmerman H.E. Angew. Chem., Int. Ed. Engl. 8 (1969) 1
37. Pincock J.A. Acc. Chem. Res. 30 (1997) 43
38. However, see:. Vancik H., Gabelica V., Rogan V., and Sunko D.E. J. Chem. Res. (S) (1990) 92