The Reaction of Ketoximes with Hypervalent Iodine Reagents: Beckmann Rearrangement and Hydrolysis to Ketones
作者:Tomohiro Maegawa、Yasuyoshi Miki、Ryohei Oishi、Ayumi Maekawa、Kazutoshi Segi、Hiromi Hamamoto、Akira Nakamura
DOI:10.1055/a-1835-2188
日期:2022.9
We investigated the reaction of ketoximes with hypervalent iodine reagents. A combination of PhI(OAc)2 and BF3·Et2O promoted the Beckmann rearrangement of ketoximes, thus yielding the corresponding amides. From a detailed investigation of the reaction, we determined that the Beckmann rearrangement is preceded by acetylation of the hydroxy group of the ketoxime in situ, accelerating the Beckmann rearrangement
我们研究了酮肟与高价碘试剂的反应。PhI(OAc) 2和BF 3 ·Et 2 O的组合促进了酮肟的贝克曼重排,从而产生了相应的酰胺。通过对反应的详细研究,我们确定贝克曼重排之前是酮肟的羟基原位乙酰化,加速了贝克曼重排。我们证实乙酰化酮肟与BF 3 ·Et 2 O 发生贝克曼重排。酮肟与Koser 试剂[PhI(OH)OTs] 在四氢呋喃存在下发生水解,在室温下以高产率提供相应的酮温度。