(The) effect of alkoxy group in radical-mediated fragmentation reactions = 라디칼 절단반응에서의 알콕시 그룹의 효과

The effect of alkoxy group in radical-mediated fragmentation reactions has been investigated. The radical-mediated fragmentation reactions of enol ethers attached to alkyl iodide with Bu$_3$SnH/AIBN afforded the mixture of nonfragmented products (reduced product and cyclized product) and fragmented products (ring-expanded product and recyclized product). Among several enol ethers attached to alkyl iodide, 7-membered silyl enol ethers gave the best results and they can be utilized as a useful method for the synthesis of different ring-sized-bicyclic compounds from initial bicycles. The comparative radical reaction of compound 19 and 28 showed that the ring-expansion via $\beta$-fragmentation can be facilitated by the presence of alkoxy group. The oxygen-centered radical-mediated fragmentation reactions of enol ethers attached to alkyl nitrate ester under radical conditions have been investigated. These enol ethers had been cleaved through the radical pathway to the ring-expanded products in relatively low yields.
Advisors
Kim, Sung-Gakresearcher김성각researcher
Publisher
한국과학기술원
Issue Date
1994
Identifier
69169/325007 / 000923042
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1994.2, [ iii, 61 p. ]

URI
http://hdl.handle.net/10203/32656
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=69169&flag=t
Appears in Collection
CH-Theses_Master(석사논문)
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