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1- and 2-(trialkylsilyl)ethanols: new silyl reagents from tin, lithium, and boron chemistry

Soderquist, John A ; Rivera, Isaac ; Negron, Alvin

Journal of organic chemistry, 1989-08, Vol.54 (17), p.4051-4055 [Periódico revisado por pares]

Washington, DC: American Chemical Society

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Título:
1- and 2-(trialkylsilyl)ethanols: new silyl reagents from tin, lithium, and boron chemistry
Autor: Soderquist, John A ; Rivera, Isaac ; Negron, Alvin
Assuntos: 400201 - Chemical & Physicochemical Properties ; ALCOHOLS ; ALKALI METALS ; BORON COMPOUNDS ; Chemistry ; DATA ; DATA ANALYSIS ; ELEMENTS ; ETHANOL ; Exact sciences and technology ; EXPERIMENTAL DATA ; HYDRIDES ; HYDROGEN COMPOUNDS ; HYDROXY COMPOUNDS ; INFORMATION ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; LITHIUM ; MEASURING INSTRUMENTS ; MEASURING METHODS ; METALS ; NUMERICAL DATA ; ORGANIC BORON COMPOUNDS ; Organic chemistry ; ORGANIC COMPOUNDS ; ORGANIC SILICON COMPOUNDS ; Organometalloidal and organometallic compounds ; Preparations and properties ; Si derivatives ; SILANES ; SILICON COMPOUNDS ; SYNTHESIS ; TIN
É parte de: Journal of organic chemistry, 1989-08, Vol.54 (17), p.4051-4055
Notas: istex:0DBE8CE5E754AAED97C2C4185E8373D992C69CFE
ark:/67375/TPS-2QVQW7N7-0
Descrição: Efficient preparations of isomerically pure 1- and 2-(trialkylsilyl)ethanols from vinylsilanes with borane reagents are described. In the former case, the borane reduction of the appropriate acetylsilane (12) gave good yields (82-94%) of the desired 1-R{sub 3}Si products (13, R = Me, Et, i-Pr). The reaction of ({alpha}-methoxyvinyl)lithium (10) (from Sn/Li exchange) with the appropriate chlorosilanes provided the corresponding ({alpha}-methoxyvinyl)silanes (11) (89-94%). Hydrolysis of 11 afforded acylsilanes (12) in excellent yield (93%). Hydroboration of the vinylsilanes (1) with 9-borabicyclo(3.3.1)nonane (9-BBN) gave ({beta}-borylethyl)silanes (2), which were oxidized to provide isomerically pure 2-silylethanols (3). The formation of Normant's reagent (4, vinylmagnesium bromide in THF) and Seyferth's reagent (7, unsolvated vinyllithium) were examined in some detail, and several new minor processes were identified. Unlike less hindered chlorosilanes, the triisopropylsilyl compound fails to react cleanly with 4, but is smoothly converted to 1c (79%) with 7. It was demonstrated that 11c (R = i-Pr) afforded 3c (89%) via a one-pot hydroboration/elimination/hydroboration/oxidation sequence. Complete, assigned {sup 13}C NMR data for these silanes are presented and compared to their trimethylsilyl counterparts.
Editor: Washington, DC: American Chemical Society
Idioma: Inglês

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1- and 2-(trialkylsilyl)ethanols: new silyl reagents from tin, lithium, and boron chemistry

Soderquist, John A ; Rivera, Isaac ; Negron, Alvin

Washington, DC: American Chemical Society

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