Synthesis and Claisen rearrangement of alkoxyallyl enol ethers. Evidence for a dipolar transition state

RM Coates, BD Rogers, SJ Hobbs…

文献索引：Coates,R.M.; Rogers,B.D.; Hobbs,S.J. Journal of the American Chemical Society, 1987 , vol. 109, p. 1160

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被引用次数: 163

摘要

Abstract: The synthesis and Claisen rearrangement of a series of 4-, 5-, and 6-alkoxyallyl vinyl ethers are reported. The 4-and 6-alkoxy derivatives (4a-d, 13, and 15) rearrange 9.5- 159 times faster than the parent allyl vinyl ethers. In addition, a significant solvent effect is observed; the rates of rearrangement of the 4-and 6-alkoxy derivatives are increased 18-68- fold upon changing from benzene to methanol, ethanol, or 80% aqueous ethanol while ...