Free radical reactions using n - tetrabutylammonium peroxydisulfate = 테트라 부틸 암모늄퍼옥시 디 술페이트를 이용한 자유 라디칼 반응

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Various allylic or benzylic alcohols were oxidized into the corresponding carbonyl compounds in the presence of n-tetrabutylammonium peroxydisulfare $((TBA)_2S_2O_8$, $(n-Bu_4N)_2S_2O_8)$ in organic solvents. Under the similar conditions allylic, benzylic, and various alcohols containing multifunctional groups were reacted with tetrabutylammonium peroxydisulfate in anhydrous THF under argon atmosphere to give 2-tetrahydrofuranyl ethers in excellent yields. The procedure for the tetrahydrofuranylation is remarkably simple and can be carried out under the mild conditions through radical coupling. $\beta$-Masked formylating products were obtained from the reactoin of electron-deficient olefins and n-tetrabutylammonium peroxydisulfate in anhydrous 1,3-dioxolane. In these reactions, 1,4-addition products were obtained in excellent yields. When various nitroolefins were reacted with tetrabutylammonium peroxydisulfate in anhydrous 1,3-dioxlane under argon atmosphere, $\alpha$-masked formylated ketones were obtained in moderate yields. In connection with the addition of 1,3-dioxolan-2-yl radical to electron-deficient olefins, these procedures were applied to a simple method for the masked acetylation of electron-deficient olefins under a nearly neutral and mild conditions. 1,4-Addition products, which were formed from the reaction of 2-methyl-1,3-dioxolan-2-yl radical and electron-deficient olefins, were also obtained in moderate yields. The addition of tetrahydrofuran to electron-deficient olefins by tetrabutylammonium peroxydisulfate has been found to result in 1,4-addition products in good yields.
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1992
Identifier
59736/325007 / 000875393
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1992.2, [ vii, 127 p. ]

URI
http://hdl.handle.net/10203/31191
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=59736&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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