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Formation of 2-vinylcyclopropanecarboxylic acid esters in reactions of alkyl diazoacetates with gaseous divinyl and synthesis of 2-ethynylcyclopropanecarboxylic acid from them

 

作者: I.E.Dolgii,   E.A.Shapiro,   O.M.Nefedov,  

 

期刊: Bulletin of the Academy of Sciences of the USSR, Division of chemical science  (Springer Available online 2004)
卷期: Volume 28, issue 6  

页码: 1197-1200

 

ISSN:0568-5230

 

年代: 2004

 

DOI:10.1007/BF00947384

 

出版商: Springer_US-Boston

 

数据来源: Springer

 

摘要:

1.Thermocatalytic reaction of alkyl diazoacetates with an excess of gaseous divinyl at atmospheric pressure proceeds with the formation of the corresponding esters of isomeric 2-vinylcyclopropanecarboxylic acids with the trans-isomer predominating. The maximum yields (∼ 50%) are obtained when methyl diazoacetate is used with CuO as the catalyst.2.A simple method for the preparation of 2-ethynylcyclopropanecarboxylic acid and its esters is proposed. It consists in the dehydrobromination with aqueous-alcoholic KOH of 2-(1,2-dibromoethyl)cyclopropanecarboxylic acid or its esters, obtained by the low-temperature bromination of 2-vinylcyclopropanecarboxylic acid or its esters.3.By the oxidative dimerization of 2-ethynylcyclopropanecarboxylic acid, the previously unknown bis (2-carboxycyclopropyl)diacetylene was obtaine

 

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