High-pressure cycloadditions of pyrones: synthesis of highly functionalized six-membered rings by inhibition of carbon dioxide loss
High-pressure cycloadditions of pyrones: synthesis of highly functionalized six-membered rings by inhibition of carbon dioxide loss
复制标题
吡喃酮的高压环加成：通过抑制二氧化碳损失合成高功能化的六元环
DOI：
10.1021/jo00445a050
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发表时间：
1977
影响因子：
3.6
通讯作者：
Y. S. Yu
中科院分区：
文献类型：
--
作者：
J. Gladysz;S. J. Lee;J. Tomasello;Y. S. Yu
通过3-羟基-2-吡喃酮(2)与各种亲双烯化合物在室温下的高压(20-40kbar)环加成反应，合成了一系列高官能化的双环加合物(3-6)。先生：加压加快了具有负活化体积的化学反应的速度，减缓了具有正活化体积的化学反应的速度。1道本最近表明，在8-20千巴范围内的压力对烯胺、二烯胺和呋喃的环加成反应是有用的。2执行大规模高压合成所需的设备只是中等价格，3使其在制备化学中的应用变得实用。
A series of highly functionalized bicyclic adducts (3-6) have been preparedvia the high-pressure (20-40 kbar) cycloaddition of 3-hydroxy-2-pyrone (2) with various dienophiles at room temperature.Sir: The application of pressure accelerates the rates of chemical reactions which have a negative volume of activation and retards the rates of those which have a positive volume of activation. 1 Dauben has recently shown that pressures in the 8-20-kbar range are useful in effecting cycloaddition re-actions of enamines, dienamines, and furans. 2 The requisite apparatus for executing large-scale high-pressure syntheses is only moderately expensive, 3 making its use practical in preparative chemistry.