Preparation of trifluoromethylated allylic and homoallylic alcohols from trifluoroacetaldehyde and organometallic compounds = $CF_3$기를 포함한 알릴릭과 호모알릴릭 알콜의 합성

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Ethyl 4, 4, 4-trifluoro-2-substituted-3-hydroxybutyrate have been synthesized by the Reformatsky-type reaction between trifluoroacetaldehyde and $\alpha$-substituted bromoacetate in tetrahydrofuran with ultrasonic irradiation. The dehydration of hydroxy esters to ethyl 4, 4, 4-trifluorocrotonate have been carried out with phosphorus pentoxide. $\alpha$-Trifluoromethylated allylic alcohols were prepared from the reduction of ester to alcohols with lithium aluminum hydride and aluminum chloride. $\alpha$-Trifluoromethylated allylic alcohols have been derived by the Grignard reaction between vinyl bromide and trifluoroacetaldehyde under ultrasonic irradiation at the mild condition. The reactions of allylmetallic compounds derived from zinc, cadmiun, manganese, chromium (II) with perfluoroaldehyde under ultrasonic irradiation resulted in the formation of homoallylic alcohols with high degree of stereoselectivity. The stereoselective synthesis of $\alpha$-trifluoromethyl allylic alcohols utilizing the hydromagnesation of 1, 1, 1-trifluoro-4-substituted-3-butyn-2-ol have been sucessfully carried out. We also have examined the phenylation of 1, 1, 1-trifluoro-3-buten-2-ol and 1, 1, 1-trifluoro-4-penten-2-ol catalyzed by palladium acetate.
Advisors
Choi, Sam-Kwon최삼권
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1983
Identifier
60790/325007 / 000785004
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1983.8, [ vii, 80 p. ]

URI
http://hdl.handle.net/10203/31234
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=60790&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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