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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