Synthesis of β,β-Difluoro-γ,δ-unsaturated Carboxylic Esters Using Claisen Rearrangement

Synlett

Volumn 1996, Issue 1, 1996, Pages 82-84

  Takagi, Toshiyuki ^a   Okikawa, Naoko ^a   Johnoshita, Shuichi ^a   Koyama, Mayumi ^a   Ando, Akira ^a   Kumadaki, Itsumaro ^a  

^a SETSUNAN UNIVERSITY   (Japan)

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Indexed keywords

EID: 0043036903     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5334     Document Type: Article

References (14)

1. Reviews: "Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications", Edited by R, Filler, Y. Kobayashi, L. M. Yagupolskii, Elsevier, Amsterdam, 1993.
2. A review on the works before 1985: I. Kumadaki, J. Pharm. Soc. Jpn., 1985, 105, 713. Concerning trifluoromethylation using trifluoromethyl copper complex, see: Y. Kobayashi, I. Kumadaki, Tetrahedron Lett., 1969, 4095; Y. Kobayashi, Y. Yamamoto, I. Kumadaki, Tetrahedron Lett., 1979, 4071.
3. A review on the works before 1985: I. Kumadaki, J. Pharm. Soc. Jpn., 1985, 105, 713. Concerning trifluoromethylation using trifluoromethyl copper complex, see: Y. Kobayashi, I. Kumadaki, Tetrahedron Lett., 1969, 4095; Y. Kobayashi, Y. Yamamoto, I. Kumadaki, Tetrahedron Lett., 1979, 4071.
4. A review on the works before 1985: I. Kumadaki, J. Pharm. Soc. Jpn., 1985, 105, 713. Concerning trifluoromethylation using trifluoromethyl copper complex, see: Y. Kobayashi, I. Kumadaki, Tetrahedron Lett., 1969, 4095; Y. Kobayashi, Y. Yamamoto, I. Kumadaki, Tetrahedron Lett., 1979, 4071.
5. Concerning the ene reaction of trifluoromethyl carbonyl compounds and their application for the syntheses of various types of fluorine compounds, see reviews; T. Nagai, I. Kumadaki, J. Synth. Org. Chem. Jpn, 1991, 49, 624; I. Kumadaki, Reviews on Heteroatom Chem., 1993, 9, 181.
6. Concerning the ene reaction of trifluoromethyl carbonyl compounds and their application for the syntheses of various types of fluorine compounds, see reviews; T. Nagai, I. Kumadaki, J. Synth. Org. Chem. Jpn, 1991, 49, 624; I. Kumadaki, Reviews on Heteroatom Chem., 1993, 9, 181.
7. T. Takagi, A. Takesue, M. Koyama, A. Ando, T. Miki, I. Kumadaki J. Org. Chem., 1992, 57, 3921.
8. T. Takagi, A. Takesue, A. Isowaki, M. Koyama, A. Ando, I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1071.
9. T. Takagi, J. Takahashi, H. Nakatsuka, M. Koyama, A. Ando, I. Kumadaki, Chem. Pharm. Bull., in Print.
10. 3) ppm: 30.34 (2F, t-d, J=14.72, 0.77 Hz).
11. 3) ppm: 30.35 (2F, t-t-d, J=14.69, 2.44, 0.98 Hz).
12. 3) ppm: 30.57 (2F, t-t-d, J=14.80, 2.32, 0.99 Hz). Structures of 8a to 8c were confirmed by their formation on acetylation of alcohols (4) with acetic anhydride and pyridine.
13. R E. Banks, "Fluorocarbons and Their Derivatives", Magdnald Technical Scientifics, London, 1970, PP.235.
14. 3) ppm: 24.020 (2F, t-q-t, J=14.96, 2.60, 2.60 Hz).