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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 26, Number 1
JKCSEZ 26(1)
February 20, 1982 

 
Title
Selective Cleavage of 2,2,2-Trichloroethyl Esters with Activated Zinc Dust in the Presence of Phthalimido Group

Phthalimido 기 존재하에서 아연분말에 의한 2,2,2-Trichloroethyl 에스테르의 선택적 환원분해
Author
Bong Young Chung, Choon Ok Maeng, Young Hwan Kim

정봉영, 맹춘옥, 김영환
Keywords
Abstract
Phthalimido기와 2, 2, 2-trichloroethyl기를 공유한 화합물들, 즉 2,2,2-trichloroethyl phthalimidoacetate (1a), 2,2,2-trichloroethyl 6-phthalimidohexanoate (2a), 2,2,2-trichloroethyl 2-phthalimidopropanoate (3a) 및 2,2,2-trichloroethyl N-phthaloylcarbamate (4a)를 합성하여 초산수용액(방법 A), THF 수용액(방법 B)및 triethylamine을 포함한 THF 수용액(방법 C)에서 아연분말과 각각 반응시킨 결과, 방법 A와 B의 경우에는 2, 2, 2-trichloroethyl기가 환원분해 됨과 동시에 phthalimido기도 3-hydroxyphthalimidino기로 환원됨을 알았으며, 방법 C의 경우에는 phthalimido기는 환원되지 않고 2, 2, 2-trichloroethyl 기 만이 선택적으로 환원 분해됨을 발견하였다.

Four 2, 2, 2-trichloroethyl esters possessing a phthalimido group, 2,2,2-trichloroethyl phthalimidoacetate (1a), 2,2,2-trichloroethyl 6-phthalimidohexanoate (2a), 2,2,2-trichloroethyl 2-phthalimidopropanoate (3a) and 2,2,2-trichloroethyl N-phthaloylcarbamate (4a) were prepared and treated with zinc dust in aqueous acetic acid(Method A), in aqueous THF(Method B), and in aqueous THF containing triethylamine (Method C). By Methods A and B, 2,2,2-trichloroethyl ester linkage of the compounds 1a, 2a and 3a was reductively cleaved with concurrent reduction of phthalimido group to a 3-hydroxyphthalimidino group. By employing Method C, however, 2,2,2-trichloroethyl ester linkage of all the four compounds was selectively cleaved while the phthalimido group was preserved.

Page
43 - 48
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