Study on the reaction of phosphonates = 포스포네이트를 이용한 반응 연구

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A method for the preparation of furylphosphonates has been developed starting with the addition of homoallylic phosphonates to nitrile, followed by a sequence consisting of acidic hydrolysis, iodine-mediated cyclization and dehydroiodination by DBU. β-Phosphonato-β,γ-unsaturated ketones have been prepared in high yields from iodocyclization of β-hydroxy phosphonates followed by treatment with t-BuOK. Treatment of lithiated homoallylic phosphonates with dimethyl carbamoyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidophosphonate in dimethoxy ethane DME-$H_2O$(2:1 vol) reacted with 2eq. iodine at room temperature to give α-phosphono-γ-iodoalkyl-γ-butyrolactones in good yield. We did not have to isolate the cis- and trans- isomers of dihydrofurans, because the stereoisomers afforded same α-methylene-γ-iodoalkyl-γ-substituted --butyrolactones by Horner-Emmons reaction. Reactions of the lithio anions derived from diethyl alkylphosphonates with phenyltellurenyl iodide gave diethyl 1-(phenyltelluro) alkylphosphonates. Diethyl 1-(alkyltelluro) phospho-nates were also prepared by the reaction of lithium tellurolates with iodomethylphosphonates. Reaction of α-lithio methylphosphonate with carbonyl compounds in THF followed by addition of diethyl chlorophosphate gave the phosphate derivatives. The phosphates were converted into the elimination product, vinylphosphonates, by treatment with t-BuOK in THF.
Advisors
Oh, Dong-Young오동영
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1996
Identifier
105357/325007 / 000935288
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1996.2, [ iii, 173 p. ]

Keywords

Iodocyclization; Wadsworth-Emmons Reaction; Phosphonate; Vinyl Telluride; 비닐텔루라이드; 요오드고리화반응; 워즈워스-에몬스 반응; 포스포네이트

URI
http://hdl.handle.net/10203/31431
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=105357&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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