[3,3]-Sigmatropic rearrangements of fluorocarbanions

作者: V.G. Andreev , A.F. Kolomiets , A.V. Fokin

DOI: 10.1016/S0022-1139(00)81173-2

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摘要: Abstract The reactions of terminal polyfluoroalkenes with 2,3-unsaturated alcohols and deprotonation the addition products these reagents under mild conditions give unsaturated fluoroaliphatic acids their derivatives. cause unusually formation compounds is spontaneous [3,3]-sigmatropic rearrangement initially formed fluorocarbanions associated elimination fluoride ion. probability realizing sigmatropic shifts determined by structural peculiarities intermediates generated.

参考文章(15)
Tsutomu Yokozawa, Takeshi Nakai, Nobuo Ishikawa, Alpha-Acylation and -allylation of β,β,β-trifluoropropionic esters via the ketene silyl acetals Tetrahedron Letters. ,vol. 25, pp. 3991- 3994 ,(1984) , 10.1016/0040-4039(84)80048-9
C.G. Krespan, Negative substituents in the claisen rearrangement Tetrahedron. ,vol. 23, pp. 4243- 4249 ,(1967) , 10.1016/S0040-4020(01)88821-9
Scott E. Denmark, Michael A. Harmata, Carbanion-accelerated Claisen rearrangements 3. Vicinal quaternary centers Tetrahedron Letters. ,vol. 25, pp. 1543- 1546 ,(1984) , 10.1016/S0040-4039(01)90005-X
Frederick E. Ziegler, The thermal, aliphatic Claisen rearrangement Chemical Reviews. ,vol. 88, pp. 1423- 1452 ,(1988) , 10.1021/CR00090A001
Jack E. Baldwin, Stephen E. Branz, Jerry A. Walker, The radical nature of the [1,3]-sigmatropic rearrangements of electron-rich olefins Journal of Organic Chemistry. ,vol. 42, pp. 4142- 4144 ,(1977) , 10.1021/JO00445A034
Scott E. Denmark, Michael A. Harmata, Carbanion-accelerated Claisen rearrangements. 2. Studies on internal asymmetric induction Journal of Organic Chemistry. ,vol. 48, pp. 3369- 3370 ,(1983) , 10.1021/JO00167A058
G. Haufe, K. Schulze, G. Alvernhe, Synthesis of monofluorinated compounds from methallyl chloride Journal of Fluorine Chemistry. ,vol. 54, pp. 263- ,(1991) , 10.1016/S0022-1139(00)83772-0
Robert J. Koshar, Thomas C. Simmons, Friedrich W. Hoffmann, The Addition of Alcohols to Octafluoroisobutene1 Journal of the American Chemical Society. ,vol. 79, pp. 1741- 1744 ,(1957) , 10.1021/JA01564A057
S. E. Denmark, M. A. Harmata, Carbanion-Accelerated Claisen Rearrangements Journal of the American Chemical Society. ,vol. 104, pp. 4972- 4974 ,(1982) , 10.1021/JA00382A051
D. A. Evans, A. M. Golob, [3,3]Sigmatropic rearrangements of 1,5-diene alkoxides. Powerful accelerating effects of the alkoxide substituent Journal of the American Chemical Society. ,vol. 97, pp. 4765- 4766 ,(1975) , 10.1021/JA00849A054