Functional rearrangement of 3-Cl or 3,3-diCl-γ-lactams bearing a secondary 1-chloroalkyl substituent at C-4

Tetrahedron

Volumn 66, Issue 6, 2010, Pages 1357-1364

  Pattarozzi, Mariella ^a   Roncaglia, Fabrizio ^a   Accorsi, Luca ^a   Parsons, Andrew F ^b   Ghelfi, Franco ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Lactams; Eliminations; Halocompound; Radical reactions; Rearrangements

Indexed keywords

ALKYL GROUP; AMIDE; CARBON; CHLORIDE; GAMMA LACTAM DERIVATIVE; HALOGEN;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; CYCLIZATION; PRIORITY JOURNAL;

EID: 73649092754     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.111     Document Type: Article

References (58)

1. Burns N.Z., Baran P.S., and Hoffmann R.W. Angew. Chem., Int. Ed. 48 (2009) 2854-2867
2. Trost B.M., and Livingston R.C. J. Am. Chem. Soc. 130 (2008) 11970-11978
3. Vora H.V., and Rovis T. J. Am. Chem. Soc. 129 (2007) 13796-13797
4. Zeitler K. Angew. Chem., Int. Ed. 44 (2005) 7506-7510
5. Nagashima H., and Itoh K. J. Synth. Org. Chem. 53 (1995) 298-307
6. Clark A.J. Chem. Soc. Rev. 31 (2002) 1-11
7. Alcaide B., Almendros P., and Luna A. Chem. Rev. 109 (2009) 3817-3858
8. Clark A.J., and Wilson P. Tetrahedron Lett. 49 (2008) 4848-4850
9. Bull J.A., Hutchings M.G., Luján C., and Quayle P. Tetrahedron Lett. 49 (2008) 1352-1356
10. Thommes K., Burçak I., Scopelliti R., and Severin K. Chem.- Eur. J. 13 (2007) 6899-6907
11. Wolf J., Thommes K., Briel O., Scopelliti R., and Severin K. Organometallics 27 (2008) 4464-4474
12. Edlin C.D., Faulkner J., Fengas D., Helliwell M., Knight C.K., House D., Parker J., Preece J., Quayle P., Raftery J., and Richards S.N. J. Organomet. Chem. 691 (2006) 5375-5382
13. Clark A.J., Geden J.V., and Thom S. J. Org. Chem. 71 (2006) 1471-1479
14. Motoyama Y., Hanada S., Shimamoto K., and Nagashima H. Tetrahedron 62 (2006) 2779-2788
15. Kawano T., Kuwana J., Shinomaru T., Diu C.-X., and Ueda I. Chem. Lett. 30 (2001) 1230-1231
16. Seigal B.A., Fajardo C., Clark A.J., Battle G.M., Heming A.M., Haddleton D.M., and Bridge A. Tetrahedron Lett. 42 (2001) 2003-2005
17. Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastécouères D., Gerard H.T., Verlhac J.-B., and Wongtap H. J. Chem. Soc., Perkin Trans. 1 (2000) 671-680
18. Clark A.J., Filik R.P., and Thomas G.H. Tetrahedron Lett. 40 (1999) 4885-4888
19. Benedetti M., Forti L., Ghelfi F., Pagnoni U.M., and Ronzoni R. Tetrahedron 53 (1997) 14031-14042 references cited here
20. Motoyama Y., Gondo M., Masuda S., Iwashita Y., and Nagashima H. Chem. Lett. 33 (2004) 442-443
21. Iwamatsu S., Kondo H., Matsubara K., and Nagashima H. Tetrahedron 55 (1999) 1687-1706
22. Nagashima H., Wakamatsu H., Ozaki N., Ishii T., Watanabe M., Tajima T., and Itoh K. J. Org. Chem. 57 (1992) 1682-1689
23. Forti L., Ghelfi F., Levizzani S., and Pagnoni U.M. Tetrahedron Lett. 40 (1999) 3233-3234
24. Baldovini N., Bertrand M.-P., Carrière A., Nougurier R., and Plancher J.-M. J. Org. Chem. 61 (1996) 3205-3208
25. Slough G.A. Tetrahedron Lett. 43 (1993) 6825-6828
26. Clark A.J., Battle G.M., and Bridge A. Tetrahedron Lett. 42 (2001) 1999-2001
27. Ishibashi H., Uemura N., Nakatani H., Okazaki M., Sato T., Nakamura N., and Ikeda M. J. Org. Chem. 58 (1993) 2360-2368
28. Seijas J.A., Vázquez-Tato M.P., Castedo L., and Estévez R.J. Tetrahedron 48 (1992) 1637-1642
29. Cagnoli R., Ghelfi F., Pagnoni U.M., Parsons A.F., and Schenetti L. Tetrahedron 59 (2003) 9951-9960
30. Ghelfi F., and Parsons A.F. J. Org. Chem. 65 (2000) 6249-6253
31. Bryans J.S., Chessum N.E.A., Huther N., Parsons A.F., and Ghelfi F. Tetrahedron 59 (2003) 6221-6231
32. Iwamatsu S., Matsubara K., and Nagashima H. J. Org. Chem. 64 (1999) 9625-9631
33. Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., and Parsons A.F. Tetrahedron 55 (1999) 5839-5852
34. Nagashima H., Ozaki N., Ishii M., Seki K., Washiyama M., and Itoh K. J. Org. Chem. 58 (1993) 464-470
35. Nagashima H., Ara K., Wakamatsu H., and Itho K. J. Chem. Soc., Chem. Commun. (1985) 518-519
36. Nagashima H., Wakamatsu H., and Itho K. J. Chem. Soc., Chem. Commun. (1984) 652-653
37. Ghelfi F., Stevens C., Laureyn I., Van Meenen E., Rogge T.M., De Buyck L., Nikitin K.V., Grandi R., Libertini M.C., Pagnoni U.M., and Schenetti L. Tetrahedron 59 (2003) 1147-1157
38. Nikitin K.V., and Andryukhova N.P. Synthesis (2001) 89-92
39. Ngwe H., Nakayama E., Higashi T., Kinoshita H., and Inomata K. Chem. Lett. (1995) 713-714
40. Anselmi C., Camparini A., and Scotton M. J. Heterocycl. Chem. 20 (1983) 687-689
41. De Buyck L., Cagnoli R., Ghelfi F., Merighi G., Mucci A., Pagnoni U.M., and Parsons A.F. Synthesis (2004) 1680-1686
42. Ghelfi F., Pattarozzi M., Roncaglia F., Parsons A.F., Felluga F., Pagnoni U.M., Valentin E., Mucci A., and Bellesia F. Synthesis (2008) 3131-3141
43. Chen X., Zheng Y., and Shen Y. Chem. Rev. 107 (2007) 1777-1830
44. Petrini M. Chem. Rev. 105 (2005) 3949-3977
45. Ghelfi, F.; Pattarozzi, M.; Roncaglia, F.; Giangiordano, V.; Parsons, A.F. Synth. Commun., 40, in press.
46. Bellesia F., Danieli C., De Buyck L., Galeazzi R., Ghelfi F., Mucci A., Orena M., Pagnoni U.M., Parsons A.F., and Roncaglia F. Tetrahedron 62 (2006) 746-757
47. De Buyck L., Danieli C., Ghelfi F., Pagnoni U.M., Parsons A.F., Pattarozzi M., and Roncaglia F. Tetrahedron 60 (2005) 2871-2877
48. Roncaglia F., Stevens C.V., Ghelfi F., Van der Steen M., Pattarozzi M., and De Buyck L. Tetrahedron 65 (2009) 1481-1487
49. Ishibashi H., Nakatani H., Iwami S., Sato T., Nakamura N., and Ikeda M. J. Chem. Soc., Chem. Commun. (1989) 1767-1769
50. Edlin C.D., Faulkner J., Helliwell M., Knight C.K., Parker J., Quayle P., and Raftery J. Tetrahedron 62 (2006) 3004-3015
51. Nagashima H., Seki K., Ozaki N., Wakamatsu H., Itoh K., Tomo Y., and Tsuji J. J. Org. Chem. 55 (1990) 985-990
52. Smith B.S., and March J. Advanced Organic Chemistry (2001), Wiley, New York, NY pp 244
53. Haval K.P., and Argade N.P. Tetrahedron 62 (2006) 3557-3563
54. Mizufune H., Nakamura M., and Mitsudera H. Tetrahedron 62 (2006) 8539-8549
55. Paternotte I., Fan H.J., Scrève P., Claesen M., Tulkens P.M., and Sonveaux E. Bioorg. Med. Chem. 9 (2001) 493-502
56. Katsumi I., Kondo H., Fuse Y., Yamashita K., Hidaka T., Hosoe K., Takeo K., Yamashita T., and Watanabe K. Chem. Pharm. Bull. 34 (1986) 1619-1627
57. Ince J., Ross T.M., Shipman M., and Slawin A.M.Z. Tetrahedron 52 (1996) 7037-7044
58. De Buyck L., Casaert F., De Lepeleire C., and Schamp N. Bull. Soc. Chim. Belg. 97 (1988) 525-533