New synthesis of α-halo-α-oximinoketones by the reactions of α-haloketones with thionitrites티오 나이트 라이트와 α-할로케톤의 반응에 의한 α-옥시미노-α-할로케톤의 새로운 합성

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A new method to synthesize $\alpha$-oximino-$\alpha$-haloketones using alkyl thionitrites was developed under mild conditions. The reactions of $\alpha$-haloketones with t-butyl thionitrite or n-butyl thionitrite in anhydrous ether containing gaseous hydrogen chloride under mild conditions ($25-35^\circ C$) afforded the corresponding oximes. In the case of using more stable t-butyl thionitrite, the better yields of oximes were obtained than using n-butyl thionitrite probably due to the instability of n-butyl thionitrite. Since the sulfurnitrogen bond of thionitrites is relatively weaker than the oxygen-nitrogen bond of nitrites and also $RS^-$ is better leaving group than $RO^-$ in the nitrosation step, thionitrites are considered to be better reagents than nitrites for the nitrosation of $\alpha$-haloketones. Undoubtedly, this reaction appears to be initiated by nitrosation on the carbon attached to halogen of $\alpha$-haloketones. Alkyl or benzyl chloromethyl ketones reacted with t-butyl thionitrite to give the corresponding oximes in good yields (80-95\%). While, in the case of aryl halomethyl ketones, the yields of oximes were low (10-40\%).
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1981
Identifier
62879/325007 / 000791239
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1981.2, [ [iii], 45 p. ]

URI
http://hdl.handle.net/10203/32296
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=62879&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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