On the interaction of silyl triflates with enamines: iminium ion formation versus silylation
作者:Vitalij V. Levin、Alexander D. Dilman、Pavel A. Belyakov、Alexander A. Korlyukov、Marina I. Struchkova、Vladimir A. Tartakovsky
DOI:10.1016/j.tetlet.2005.03.144
日期:2005.5
The interaction of Me3SiOTf and (C6F5)3SiOTf with enamines generating α-silyl-substituted iminium ions is investigated. A trimethylsilyl iminium cation is formed as a long-lived species observable by NMR spectroscopy, whilst the tris(pentafluorophenyl)silyl analogue is very labile and prone to the loss of a proton. On the basis of the latter phenomenon, a method for the synthesis of β-silyl enamines
研究了Me 3 SiOTf和(C 6 F 5)3 SiOTf与生成α-甲硅烷基取代的亚胺离子的烯胺的相互作用。可以通过NMR光谱观察到长寿命的物种是三甲基甲硅烷基亚胺阳离子,而三(五氟苯基)甲硅烷基类似物非常不稳定,容易发生质子损失。基于后一种现象,提出了一种合成β-甲硅烷基烯胺的方法。