Fluorinative ring-contraction of cyclic alkenes with p-iodotoluene difluoride

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2589-2592

  Hara, Shoji ^a   Nakahigashi, Jun ^a   Ishi i, Kenji ^a   Fukuhara, Tsuyoshi ^a   Yoneda, Norihiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; TOLUENE DERIVATIVE;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; FLUORESCENCE SPECTROSCOPY; FLUORINATION; NONHUMAN; REACTION ANALYSIS;

EID: 0032559952     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00276-7     Document Type: Article

References (13)

1. 1. a) Carpenter, W. J. Org. Chem., 1966, 31, 2688-2689.
2. b) Zupan, M.; Pollak, A. J. Chem. Soc. Chem. Commun., 1975, 715-716.
3. c) Gregorcic, A.; Zupan, M. Bull. Chem. Soc. Jpn., 1976, 50, 517-520.
4. d) Gregorcic, A.; Zupan, M. J. Chem. Soc. Perkin I, 1977, 1446-1449.
5. e) Patrick, T. B.; Scheibel, J. J.; Hall, W. E.; Lee, Y. H. J. Org. Chem., 1980, 45, 4492-4494.
6. f) Sket, B.; Zupan, M.; Zupet, P. Tetrahedron, 1984, 40, 1603-1606.
7. 1f from the reaction of iodoarene difluoride with exo-or endo-cyclic alkenes, the expected ring expanded or contracted products could not be obtained.
8. 3. Hara, S.; Sekiguchi, M.; Ohmori, A.; Fukuhara, T.; Yoneda, N. J. Chem. Soc. Chem. Commun., 1996, 1899-1900; Hara, S.; Hatakeyama, T.; Chen, S.-Q.; Ishi-i, K.; Yoshida, M.; Sawaguchi, M.; Fukuhara, T.; Yoneda, N. J. Fluorine Chem., 1997, in press.
9. 3. Hara, S.; Sekiguchi, M.; Ohmori, A.; Fukuhara, T.; Yoneda, N. J. Chem. Soc. Chem. Commun., 1996, 1899-1900; Hara, S.; Hatakeyama, T.; Chen, S.-Q.; Ishi-i, K.; Yoshida, M.; Sawaguchi, M.; Fukuhara, T.; Yoneda, N. J. Fluorine Chem., 1997, in press.
10. 1H NMR. (equation presented)
11. 5. From cyclohexene derivatives without a methyl group on the double bond such as ethyl 3-cyclohexene-1-carboxylate, the ring-contracted products could not be obtained at all.
12. 6. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry. Chapter 6. Pergamon Press: Oxford, 1983; Ferraz, H. M. C.; Silva Jr., L. F. Tetrahedron Lett., 1997, 38, 1899-1902.
13. 6. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry. Chapter 6. Pergamon Press: Oxford, 1983; Ferraz, H. M. C.; Silva Jr., L. F. Tetrahedron Lett., 1997, 38, 1899-1902.