Synthesis of γ-lactones and unsaturated bis γ-lactones via Cu-Fe-mediated reductive cyclization of di- and tri-α-halogenated carboxylic esters

Journal of Organometallic Chemistry

Volumn 601, Issue 1, 2000, Pages 153-159

  Somech, Iris ^a   Shvo, Youval ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Bis lactones; Cu; Fe; Reductive cyclization; Chloro esters; Butyrolactones

Indexed keywords

EID: 0038364413     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00056-5     Document Type: Article

References (19)

1. M. Ascher, D. Vofsi, Chem. Soc. (1963) 1887.
2. Matsumoto H., Nikaido T., Nagai M. J. Org. Chem. 41:1976;396.
3. (a) M.S. Kharasch, W.H. Urry, E.V. Jensen, J. Am. Chem. Soc. 67 (1945) 1626.
4. (b) M.S. Kharasch, O. Reinmuth, W.H. Urry, J. Am. Chem. Soc. 69 (1947) 69, 1105.
5. (a) R. Davis, I.F. Groves, J. Chem. Soc. Dalton Trans. (1982) 2281.
6. (b) W.J. Bland, R. Davis, J.L. Durrant, J. Organomet. Chem. C75 (1984) 260.
7. Forti L., Ghelfi F., Libertini E., Pagnoni U.M., Soragni E. Tetrahedron. 53:1997;17 761. and Refs. cited therein.
8. Narkano T., Kayama M., Nagai Y Bull. Chem. Soc. Jpn. 60:1987;1049.
9. Corina A., Folli U., Sbardellati S., Taddei F. J. Chem. Soc. Perkin Trans. 2:1993;1847.
10. Schmitz A., Kraatz U., Korte F. Chem. Ber. 108:1975;1010.
11. Weinstock J.J. Am. Chem. Soc. 78:1956;4967.
12. Nagarajan A., Porchezhiyan V. Indian J. Chem. Sect. B. 24:1985;1202.
13. (a) R.P.Linstead, E.M. Mead, J. Chem. Soc. (1934) 935.
14. (b) M.S. Kharasch, P.S. Skell, P. Fisher, J. Am. Chem. Soc. 70 (1948) 1055.
15. Pietrasanta Y., Rabat J.P., Vernet J.L. Eur. Polymer J. 10:1974;639.
16. G. Midgley, C.B.Thomas, J. Chem. Soc. Perkin Trans. II (1984) 1537.
17. Ballini R., Petrini M., Rosini G. Synthesis. 8:1987;711.
18. House H.O., Babad H., Toothill R.B., Noltes A.W. J. Org. Chem. 27:1962;4141.
19. Kikukawa K., Sakai K., Asada K., Matsuda T. J. Organomet. Chem. 77:1974;131.