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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 27, Number 6
JKCSEZ 27(6)
December 20, 1983 

Synthesis of 2,4-Dienoic Acid Derivatives by Palladium Catalyzed Homogeneous Reaction

팔라듐 촉매 균일계 반응을 이용한 2,4-디엔산 유도체의 합성
Jin Il Kim

여러가지 브롬화비닐 화합물들 ((Z)-1-bromopropene, 1-bromo-2-methylpropene, 2-bromo-3-methyl-2-butene, (E)-ethyl 2-methyl-3-bromo-2-propenoate, 1-bromo-cyclohexene)과 올레핀 화합물인 ethyl acrylate, methyl methacrylate, ethyl crotonate, allyl cyanide, ethyl 3-butenoate, ethyl 4-pentenoate와 methyl 10-undecenoate를 palladium acetate촉매와 triorthotolyphosphine 및 triehylamine존재 하의 수득율로 얻었으며 이들 생성물의 입체화학도 규명하였다. 위의 방법을 이용하므로써 ethyl 3-butenoate, ethyl 4-pentenoate와 methyl 10-undecenoate에 의한 4개, 5개 및 11개 탄소-탄소 결합의 확장도 가능하였다.

A wide variety of vinylic bromides such as (Z)-1-bromopropene, 1-bromo-2-methylpropene, 2-bromo-3-methyl-2-butene, (E)-ethyl 2-methyl-3-bromo-2-propenoate, 1-bromo-cyclohexene has been found to react with ethyl acrylate, ethyl 3-butenoate, allyl cyanide, (E)-ethyl crotonate, ethyl 4-pentenoate, methyl 10-undecenoate and methyl methacrylate in the presence of triethylamine and a palladium acetate-triorthotolylphosphine catalyst. In general, 2,4-dienoic acid derivatives were obtained in good yield and stereochemistry of the products was determined. Using this method, four, five and eleven carbon-carbon extension with ethyl 3-butenoate, ethyl 4-pentenoate and methyl 10-undecenoate was also possible.

441 - 448
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