The electrocatalytic isomerisation of epoxides is observed anodically in acetonitrile free from strong nucleophiles; the electrochemically inducedisomerisation and the similar isomerisation caused by strong acids are compared.
A Convenient Method for the Preparation of Ethers from Epoxides. Trityl Hexafluoroantimonate-Catalyzed Sequential Reactions, Rearrangement and Reductive Condensation, of Epoxides
作者:Tsunehiro Harada、Teruaki Mukaiyama
DOI:10.1246/cl.1992.1901
日期:1992.10
In the presence of a catalytic amount of trityl hexafluoroantimonate, sequential reactions, rearrangement and reductive condensation, of epoxides proceed smoothly to give the corresponding ethers in fairly good yields. Trityl hexafluoroantimonate (5 mol%) efficiently accelerates the above two sequential reactions.
Treatment of pinacol monoacetate with organoaluminium reagent R3Al caused the rearrangement under uptake of R as a nucleophile on the resulting carbonyl carbon, while R2AlSPh produced the pinacolone itself upon workup.
用有机铝试剂 R3Al 处理频哪醇单乙酸酯导致在 R 作为亲核试剂在所得羰基碳上吸收时发生重排,而 R2AlSPh 在处理后产生频哪醇本身。
Nagaki, Aiichiro; Takizawa, Eiji; Yoshida, Jun-ichi, Journal of the American Chemical Society, 2009, vol. 131, p. 1654 - 1655