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Studies on Synthesis of the Thiophenes and Applications

Author: TianCui
Tutor: ZhaoYuLong；ShaoYun
School: Northeast Normal University
Course: Organic Chemistry
Keywords: Ethyl diazoacetata α-oxo ketene dithioacetal Copper(Ⅱ) trifluoromethanesulfonate Thiophene Thieno[2,3,b]thiopyran
CLC: O621.25
Type: Master's thesis
Year: 2011
Downloads: 81
Quote: 1
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Abstract


The carbon atom of ethyl diazoacetate is not only electrophilic and nucleophilic, but also is a dipolar ion, so the reaction about it is varied. Alkylation reaction happens when Ethyl diazoacetate reacts with alcohol, phenol, carboxylic acid, amine. Besides, Ethyl diazoacetate can also react with aldehydes or ketones to produce ketones which have one more methylene group. Carbenoid is produced from ethyl diazoacetate in the presence of light, heat or a catalyst and insertion or cyclization reaction can occur according to the different reaction conditions.α-oxo ketene dithioacetal, as a very important intermediate by organic synthesis, has a place in organic chemistry because the variety of functional group ensures the diversity of chemical reaction of compound of this kind. In addition, various types of reaction which include aromatization, cyclization, reduction, condensation and so on can be reacted. Based on the features of ethyl diazoacetate andα-oxo ketene dithioacetal, and aimed at developing a new way of synthetic reaction, a novel and efficient route to cyclobutenones for synthesis of thiophene has been developed. In my paper, my research mainly includes the following two aspects:1: Copper(Ⅱtrifluoromethanesulfonate-catalyzed reaction ofα-oxo ketenedithioacetal with ethyl diazoacetate offers an efficient direct route to thiophene.2: Thieno[2,3,b]thiopyran was synthesized from thiophene.In my paper, 22 compounds were synthesized and confirmed by 1HNMR and 13CNMR spectroscopies, etc.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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