The Reaction Of Aldoximes With NaCl And Oxone Under Ball-Milling Conditions

In recent years,mechanochemistry,which is well-known in the fields of crystal engineering and polymorphism,has reappeared in the vision of scientists as a technique applied to organic synthesis.As well known,the activation methods commonly used in traditional chemical reactions mainly include thermal heating,photoirradiation and electrochemical methods.Therefore,mechanochemistry is a supplement to traditional activation methods.As a new synthetic technology,mechanochemistry has attracted more and more attention from scientists because of its solvent-free characteristics in line with the concept of green chemistry,and is widely used in the synthesis of various organic molecules.It not only has the advantages of shortening the chemical reaction time and improving the efficiency of the chemical reaction,but also it can change the chemical reactivity in some cases.By changing the kinetics and thermodynamics of the reaction,different products may be obtained compared to the solution solution-phase reactions.In this regard,mechanochemistry provides an opportunity to explore new chemical reaction spaces.Hence,it is of great significance to find more reactions where mechanical grinding conditions change chemical reactivity.However,few examples on this aspect have been reported so far.This thesis focuses on the mechanochemical reaction of aldoximes with NaCl and Oxone:aldoximes react with NaCl and Oxone in the presence of the base under ball-milling conditions for 30 min to afford N-acyloxyimide chloride compounds.However,the same reation in solution mainly gives hydroxamyl chloride compounds.In anther word,a new process of mechanical ball-milling conditions to change the chemical reactivity is achieved.The raw materials used in this reaction are cheap and readily available.Morever,the reaction has good substrate adaptability and functional group compatibility.In addition,a possible mechanism for the reaction is proposed based on the control experiments.At last,it is found that for oxadiazole oxides can be obtained in good yields from benzaldehyde oximes substituted by the p-OMe,p-NO2 or p-CO2Me group and several aliphatic aldoximes by changing the reaction conditions.