Fluorinative Beckmann Fragmentation: Fluorinative .ALPHA.-Cleavage of Cyclic Ketoximes by Diethylaminosulfur Trifluoride.
作者:Masayuki KIRIHARA、Kanako NIIMI、Maiko OKUMURA、Takefumi MOMOSE
DOI:10.1248/cpb.48.220
日期:——
Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. However, the introduction of a sulfur functionality, which can stabilize a carbocation and can be easily removed from the reaction products, into the
二乙基氨基三氟化硫与带有取代基的环状酮肟反应,该取代基可以稳定碳正离子,引起氟化片段化,提供氟化腈。缺乏此类取代基的酮肟可提供复杂的混合物。然而,将可以稳定碳正离子并且可以容易地从反应产物中除去的硫官能度引入到酮肟中对于产生氟化碎片是有效的。