서지주요정보
Study on the reaction of phosphonates = 포스포네이트를 이용한 반응 연구
서명 / 저자 Study on the reaction of phosphonates = 포스포네이트를 이용한 반응 연구 / Chi-Wan Lee.
저자명 Lee, Chi-Wan ; 이치완
발행사항 [대전 : 한국과학기술원, 1996].
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8006662

소장위치/청구기호

학술문화관(문화관) 보존서고

DCH 96013

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초록정보

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.

서지기타정보

서지기타정보
청구기호 {DCH 96013
형태사항 iii, 173 p. : 삽도 ; 26 cm
언어 영어
일반주기 Includes appendix
저자명의 한글표기 : 이치완
지도교수의 영문표기 : Dong-Young Oh
지도교수의 한글표기 : 오동영
수록 잡지명 : "t-BuOK-induced cleavage of ihydrofuran derivatives". The Journal of Organic Chemistry. American Chemical Society, vol. 60, no. 21, pp. 7027-7029
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 126-146
주제 Phosphonate
Wadsworth-Emmons Reaction
Iodocyclization
Vinyl Telluride
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