Radical reaction of oxime ether derivatives = 옥심에테르 유도체를 이용한 라디칼 반응

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The intermolecular addition of alkyl iodides to phenylsulfonyl oxime ether derivatives afforded the aldehydes, ketones, α-keto ester and 1,2-diketone in good yield. The various carbocyclic ketones, and acyclic ketones via sequential radical acylation approach using bis-methylsulfonyl oxime ether were prepared. The radical acylation reaction of O-bensyl-3-iodo-1-methylsulfonyl-propanaldoxime or O-benzyl-4-iodo-1-methylsulfonyl-butanaldoxime with alkene and hexamethylditin afforded α-substituted 5-and 6-membered cyclic ketone in good yield. Radical acylation reaction with alkyne the acylating compounds, so we could obtaine α,β-unsaturated cyclic oxime and protected lactam. All oxime ethers were easily hydrolyzed to the corresponding ketone under acidic condition. Bis-methylsulfonyl oxime ether reacted with various nucleophiles such as: enolates of esters, ketones and α-anions of sulfone. Radical acylation reactions of alkyl iodides with the substituted methylsulfonyl oxime ethers were proceded smoothly, yielding β-keto ester, 1,3-diketone, protected β-keto sulfone and protected lactone through radical acylation reaction.
Advisors
Kim, Sung-Gakresearcher김성각researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1999
Identifier
151661/325007 / 000973058
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1999.2, [ iii, 57 p. ]

Keywords

Radical cyclization; Oxime ether derivatives; β-Keto ester; β-케토 에스터; 라디칼 고리화반응; 옥심에테르 유도체

URI
http://hdl.handle.net/10203/31802
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=151661&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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