The Research Of Beckmann Rearrangement Reaction Of α, β-unsaturated Oxime Induced By Perfluoroalkyl Sulfonyl Fluoride Under Alkaline Conditions

Beckmann rearrangement reaction is is one of most familiar and classicrearrangement reaction of carbocation rearrangement reaction type. It is widely usedin organic synthesis and synthetic drugs among the large-scale industrial synthesis ofcaprolactam ring is to use the Beckmann rearrangement to complete, so researchBeckmann rearrangement reaction, rich Beckmann rearrangement reaction conditionshave important practical significance.. During the study, we found that by using aperfluoroalkyl sulfonyl fluoride induced in Beckmann rearrangement reaction underbasic conditions can be obtained not only the traditional amide, utilize unsaturatedketones can also be used for the synthesis of oxime N-alkenyl amide and there are alot of N-alkenyl amides in the conventional drugs. Also, because of our reactionsystem was alkaline, substrate contain acid-sensitive substrates group also could carryBeckmann rearrangement reaction. With fluoroalkyl sulfonyl fluoride induced underalkaline conditions, Beckmann rearrangement reaction has low cost, mild conditions,simple operation, with good usability. So our research greatly enriched the Beckmannrearrangement reaction.In this paper, we have a comprehensive study of the Beckmann rearrangementreaction conditions, the scope and and synthetic processes. The thesis is divided intothree chapters.The first chapter introduces the research progress and response characteristicsof Beckmann rearrangement, Applied Research Review perfluoroalkanesulfonylfluoride and N-alkenyl amide synthesis are reviewed.The second chapter, a comprehensive study by halothane fluoride inducedBeckmann rearrangement reaction under alkaline conditions of synthesis. After athorough investigation we found, Beckmann rearrangement reaction the most suitabletemperature is17℃, and RfSO2F/DBU/CH3Cl system to achieve the best responseeffect. The reaction is rapid, completed in a short time. In addition, substrate:RfSO2F: DBU=1:1.5:3is the best material ratio.The third chapter, we select some different substrates to synthesis of N-alkenylamide.