Synthesis of phenyl and ester substituted vinyl fluorides via reduction and olefination of esters

Article abstract of DOI:10.1080/10426509808035739

A reduction-olefination sequence has been used to convert ethyl pentafluoropropanoate 6 to 1-fluoro-1-phenyl-2-pentafluoroethyl ethene 7 and ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 8. Addition of lithium diethyl α-fluorobenzylphosphonate [(EtO)₂P(O)CFPh]^- Li⁺ 4 or lithium fluorocarboethoxymethylene dialkylphosphonate [(RO)₂P(O)CFCO₂Et]^- Li⁺ 5 (R = Et, i-Pr) to a THF solution of fluorinated aldehydes prepared in situ from 6 and diisobutylaluminum hydride (DIBAL) affords the vinyl fluorides C₂F₅CH=CFPh 7 and C₂F₅CH=CFCO₂Et 8 in good yields. However, yields of the final products 7 and 8 are low when in situ reduction of 6 to aldehyde was performed in the presence of lithium salts of 4 or 5.

Full text of DOI:10.1080/10426509808035739

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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SYNTHESIS OF PHENYL AND ESTER
SUBSTITUTED VINYL FLUORIDES VIA
REDUCTION AND OLEFINATION OF ESTERS
Hou-jen Tsai a & Donald J. Burton b
a Department of Applied Chemistry , Chung Cheng Institute of
Technology , Ta-hsi, Tao-yuan, Taiwan, R. O. C.
b Department of Chemistry , University of Iowa , Iowa City, IA52242, USA
Published online: 24 Sep 2006.
To cite this article: Hou-jen Tsai & Donald J. Burton (1998) SYNTHESIS OF PHENYL AND ESTER
SUBSTITUTED VINYL FLUORIDES VIA REDUCTION AND OLEFINATION OF ESTERS, Phosphorus, Sulfur, and
Silicon and the Related Elements, 140:1, 135-145, DOI: 10.1080/10426509808035739
To link to this article: http://dx.doi.org/10.1080/10426509808035739
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