Synthesis of vinylic tellurides and synthetic applications = 바이닐 텔루라이드의 합성 및 유기합성에의 응용

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To a solution of alkenyl zirconocene, which was conveniently generated in situ by the hydrozirconation of alkyne, was added phenyltellurenyl iodide. After hydrolysis, E-vinylic tellurides were isolated. Hydrozirconation of acetylenic tellurides afforded the first examples of 1, 1-bimetalloalkenes of tellurium and zirconium. Z-vinylic tellurides were obtained after hydrolysis of these intermediates. These 1,1-bimetalloakenes reacted with acyl halides to obtain (Z)-α-organotelluro-α,β-unsaturated carbonyl compounds via Zr-Cu transmetalation. Ketene organyltelluroacetals were obtained stereoselectively by the hydrozirconation of acetylenic tellurides and then transmetalation using organyltellurenyl iodides. Transmetalation of ketene telluroacetals was performed by using n-BuLi. 1,1-Bimetalloalkenes of Sn/Te and Sn/Se were obtained stereoselectively by the hydrozirconation of acetylenic stannanes and then transmetalation using organyltellurenyl iodides or phenylselenenyl bromide. Transmetalation of 1,1-Bimetalloalkenes of Sn/Te and Sn/Se was performed by using n-BuLi. Trans metalation of 1-trialkylstannylvinylic selenides shows very high yields and stereospecificity with electrophiles. Reaction of zirconacyclopentadienes with phenyltellurenyl iodide gave tellurophene via unusual rearrangement of zirconium complex. 1-Substituted (1E, 3E)-1,3-butadienyl phenyl tellurides and internal vinylic tellurides were synthesized stereoselectively using the preferential migration of the alkenyl or alkyl group from boron to the adjacent alkynyl carbon atom.
Advisors
Oh, Dong-Young오동영
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1997
Identifier
128464/325007 / 000945206
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1997.8, [ iii, 108 p. ]

Keywords

Hydrozirconation; Tellurium compound; Vinylic telluride; Transmetalation; 트랜스 메탈레이션; 하이드로지르코네이션; 텔루리움 화합물; 바이닐 텔루라이드

URI
http://hdl.handle.net/10203/31465
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=128464&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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