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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 9, Number 2
JKCSEZ 9(2)
April 20, 1965 

 
Title
Halogen Containing Heterocyclic Compounds (Part Ⅱ) Halogenation of Furfuryl Derivatives-Maleic Anhydride Adduct

함할로겐 이원소환화합물에 관한 연구 (제2보) 풀퍼릴유도체-마레인산무수물 부가물의 할로겐화반응
Author
You Sun Kim, Chung Hee Kim

김유선, 김정희
Keywords
Abstract
퓨란, 초산풀퍼릴, 풀퍼릴알코올과 마레인산무수물을 에틸 에테르 존재하에서 부가반응시켜 exo부가물을 만들고 이 화합물들에 대한 취소화반응을 물 존재하에서 행한 바 각각 모노부롬화락톤 및 디브롬산을 생성하였으며 락톤의 생성수율은 전위된 carbonium ion에 대한 carboxylic acid 의 반응기여(participation)에 의하여 결정되면 화합물 자체의 입체조건(steric requirement)이 그 기여에 영향을 준다는 것을 구명하였다. 퓨란부가물을 유기용매(사염화탄소, 메틸렌크로라이드0존재하에서 취소화반응하면 2취화물이 생성하고 광선 존재하에서 염기화반응하면 사염화반응물이 생성됨을 구명하였다. 각 화합물의 합성방식 및 반응과정에 관하여 논급하였다.

The exo adduct between furfuryl derivatives (furan, furfuryl acetate and furfuryl alcohol) and maleic anhydride were prepared in the presence of ethyl ether. The bromination of the exo adduct of each derivatives gave a monobromolactone and dibromoacid when the reaction was done in the presence of water. The formation of the bromolactone was proved to be dependent to the carboxylic participation to the incipient rearranged carbonium ion of a classical type, and the participation was sterically hindered by the steric structure of the substituents. The bromination of the furan-maleic anhydride adduct in the presence of organic solvent (CCl4, CH2Cl2) gave the dibromide, whereas the photochlorination of the same adduct in the presence of carbon tetrachloride gave the tetrachloride. The procedure of the preparation and the reaction path of the halogenation were described.

Page
88 - 95
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