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Nucleophilic substitution and Claisen rearrangement reactions of model fluoroalkenes of general structure R-CF=CF-CF₃

Cooper, J.A.; Olivares, C.M.; Sandford, G.

Authors

J.A. Cooper

C.M. Olivares

G. Sandford



Abstract

Fluoroalkenes of general structure R-CF=CF-CF3 (2a, R = cyclopentyl and 2b, R = cyclohexyl), prepared in high yield in two steps from hexafluoropropene and the appropriate cycloalkane, react with oxygen, carbon, and hydrogen nucleophiles to give R-CX=CF-CF3 derivatives (X = H, OR, R, Ar). Reaction of fluoroalkenes 2a and 2b with allylic alkoxides gave products arising from Claisen rearrangement, providing access to keto-alkenes bearing >CFCF3 units in mid-aliphatic chain positions.

Citation

Cooper, J., Olivares, C., & Sandford, G. (2001). Nucleophilic substitution and Claisen rearrangement reactions of model fluoroalkenes of general structure R-CF=CF-CF₃. Journal of Organic Chemistry, 66(14), 4887-4891. https://doi.org/10.1021/jo0103118

Journal Article Type Article
Publication Date Jun 1, 2001
Deposit Date May 14, 2007
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 66
Issue 14
Pages 4887-4891
DOI https://doi.org/10.1021/jo0103118

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