Negative substituents in the claisen rearrangement

作者: C.G. Krespan

DOI: 10.1016/S0040-4020(01)88821-9

关键词:

摘要: Abstract Several instances of the Claisen rearrangement are demonstrated with allyl vinyl ethers in which segment is heavily substituted negative groups. With fluoro, fluoroalkyl, chloro and alkoxy as substituents, these reactions proceed unusual ease at 25–100°. A related isomerization a propargyl ether to an allenyl ketone also described.

参考文章(16)
Jack W. Ralls, Robert E. Lundin, Glen F. Bailey, Preparation and Thermal Rearrangement of Alkenyl 3-Alkenyloxy-2-butenoates. Catalysis of the Aliphatic Claisen Rearrangement by Ammonium Chloride Journal of Organic Chemistry. ,vol. 28, pp. 3521- 3526 ,(1963) , 10.1021/JO01047A061
D. N. Matthews, Ernest I. Becker, A Contribution to the Mechanism of the Diels—Alder Reaction Journal of Organic Chemistry. ,vol. 31, pp. 1135- 1140 ,(1966) , 10.1021/JO01342A035
Calvin A. VanderWerf, Victor L. Heasley, Studies on the Preparation and Rearrangements of Allylic Azides1 The Journal of Organic Chemistry. ,vol. 31, pp. 3534- 3537 ,(1966) , 10.1021/JO01349A016
N. B. LORETTE, W. L. HOWARD, The Cracking and Rearrangement of Diallyl Ketals to α-Allyl Ketones Journal of Organic Chemistry. ,vol. 26, pp. 3112- 3115 ,(1961) , 10.1021/JO01067A017
Samuel F. Reed, The Facile Rearrangement of Vinyl 3-(Penta-1,4-dienyl) Ether Journal of Organic Chemistry. ,vol. 30, pp. 1663- 1665 ,(1965) , 10.1021/JO01016A515
S. M. McElvain, Harrison I. Anthes, Sydney H. Shapiro, Ketene Acetals. XI. The Pyrolysis of Ketene Acetals and Orthoesters Journal of the American Chemical Society. ,vol. 64, pp. 2525- 2531 ,(1942) , 10.1021/JA01263A001
Harlan L. Goering, Robert R. Jacobson, A Kinetic Study of the ortho-Claisen Rearrangement1 Journal of the American Chemical Society. ,vol. 80, pp. 3277- 3285 ,(1958) , 10.1021/JA01546A024
Lawrence Stein, George W. Murphy, Kinetics of the Rearrangement of Isopropenyl Allyl Ether1 Journal of the American Chemical Society. ,vol. 74, pp. 1041- 1043 ,(1952) , 10.1021/JA01124A050
R. B. Woodward, Roald Hoffmann, Selection Rules for Sigmatropic Reactions Journal of the American Chemical Society. ,vol. 87, pp. 2511- 2513 ,(1965) , 10.1021/JA01089A050
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