An unexpected equilibrium process associated with a standard approach to ynone synthesis
An unexpected equilibrium process associated with a standard approach to ynone synthesis
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DOI：
10.1021/jo025682i
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发表时间：
2002-07-12
影响因子：
3.6
通讯作者：
Roberts, JC
中科院分区：
文献类型：
--
作者：
Jackson, MM;Leverett, C;Roberts, JC
直接比较了Weinreb酰胺和吗啉酰胺与炔基锂试剂生成酮的反应。在Weinreb酰胺的情况下，用化学计量比的炔基锂处理通常会发生完全反应，而相应的吗啉酰胺则会发生不完全反应。这种差异归因于后一种情况下的意外平衡过程，并表明过量的炔基锂试剂与吗啉、酰胺一起使用提供了一种在0℃合成芳酮的合成有用的方法。
A direct comparison between Weinreb amides and morpholine amides was made with regard to their reactions with alkynyllithium reagents to form ynones. While treatment with stoichiometric alkynyllithium generally effects complete reaction in the case of Weinreb amides, incomplete reactions are obtained from the corresponding morpholine amides. This difference is attributed to an unexpected equilibrium process in the latter case, and it is shown that the use of excess alkynyllithium reagent with morpholine, amides provides a synthetically useful synthesis of ynones at 0 degreesC.