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Construction Of Benzosulfonimide Derivatives By Tandem Cyclization/SO2 Insertion Reaction Of N-Cyanamide Olefins Involving Sodium Metabisulfite

Posted on:2024-04-17Degree:MasterType:Thesis
Country:ChinaCandidate:Y H WuFull Text:PDF
GTID:2531307064982189Subject:Organic Chemistry
Abstract/Summary:
Sulfonyl compounds have very important roles in biology,medicine,materials and other fields.In recent years,the method of introducing sulfonyl groups into organic molecules by SO2 substitution has gradually become an important means of synthesizing sulfonyl compounds.In this paper,we develop a strategy for the construction of benzosulfonimide derivatives by tandem cyclization of radicals with N-cyanoalkenes under green and mild conditions through SO2 insertion,where the inorganic SO2 substitute"Na2S2O5"is used as both a reducing agent and a source of SO2 in the system.The main points of this paper are summarized as follows:Part Ⅰ:we focus on the application of SO2 substitution,which plays a reducing role in the system,to the synthesis of sulfonyl compounds and elaborate on the intention of this paper.Part Ⅱ:we have described the common methods for the synthesis of benzosulfonimide derivatives.And the fluoroalkyl-substituted benzosulfonimides were successfully constructed by the tandem cyclization/SO2 insertion reaction of fluoroalkyl radicals with N-cyanamide olefins.The utility of the reaction was also verified by amplification and conversion experiments.In addition to this,we also made a preliminary exploration of whether other radical precursors can be used to obtain the corresponding benzosulfonimides under this condition,where aryl diazonium salts were used as a radical source,and we also achieved double SO2 insertion.
Keywords/Search Tags:sodium metabisulfite, radicals, tandem reaction, SO2 insertion, sulfonamide
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