- Convenient Synthesis of Functionalized Dialkyl Ketones and Alkanoylsilanes: 1-(Benzotriazol-1-yl)-1-phenoxyalkanes as Alkanoyl Anion Equivalents
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(Benzotriazol-1-yl)-1-phenoxyalkanes 10, prepared by two-step transformations of the corresponding aldehydes, are readily deprotonated at the methine group by BuLi.Subsequent reactions with alkyl halides, aldehydes, ketones, and imines yield the corresponding substituted derivatives that undergo hydrolysis under acidic conditions to afford the expected functionalized ketones 13, 15, 17, 19, 21, 24 and 25.Two successive lithiations of (benzotriazolyl)phenoxymethane, each followed by reaction with a trialkylsilyl chloride, alkyl halide, aldehyde, or ketone, generate similar intermediates 27, 39, 31, 33, and 36.Subsequent hydrolyses of 27, 29, 31, 33, and 36 yield the functionalized ketones 28, 30, and 32 and the alkanoylsilanes 34 and 37 in good yields.
- Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Lie, Zhu
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p. 7551 - 7557
(2007/10/03)
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- Counterattack Reagent: Hexamethyldisilane in a Direct Synthesis of Ketene Dithioacetals and 2-Trimethylsilyl-1,3-dithiane Derivatives from 1,3-Dithiane
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A novel method has been developed for the direct synthesis of ketene dithioacetals and 2-trimethylsilyl-1,3-dithiane derivatives from 1,3-dithiane.Treatment of 1,3-dithiane (1.0 mol equiv.) with BuLi (1.1 mol equiv.), HMPA (4.0 mol equiv.), and Me3SiSiMe3
- Hwu, Jih Ru,Lee, Taekyo,Gilbert, Bryant A.
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p. 3219 - 3224
(2007/10/02)
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