Cooper, J. A. and Olivares, C. M. and 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). pp. 4887-4891.
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.
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|Publisher Web site:||http://dx.doi.org/10.1021/jo0103118|
|Record Created:||14 May 2007|
|Last Modified:||08 Apr 2009 16:31|
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