Chinese Journal of Organic Chemistry >
K2S2O8/H2O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides
Received date: 2018-01-18
Revised date: 2018-03-19
Online published: 2018-04-04
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.
Under neutral reaction conditions, sodium triflate promotes the radical reaction of potassium persulfate with water to yield a proton which induces Schmidt rearrangement of alkenyl azides. A variety of substituted acetanilide compounds were synthesized in one step. To obtain the optimal reaction conditions, an arrange of reaction parameters such as radical initiator, solvent, temperature, and reaction time have been screened. This reaction features an easy accessibility of starting materials, simple operation, broad substrate scope and so on. We finally proposed the plausible mechanism based on the mechanistic studies and previous literature.
Key words： vinyl azides; acetanilides; radical reaction; Schmidt rearrangement
Xu Zheng , Zhou Bingwei , Jin Hongwei , Liu Yunkui . K2S2O8/H2O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1823 -1828 . DOI: 10.6023/cjoc201801025
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