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• W2065902955 endingPage "4975" @default.
• W2065902955 startingPage "4965" @default.
• W2065902955 abstract "N-Lithio-N-(trialkylsilyl)allylamines can be deprotonated in the presence of ethereal solvents exclusively at the cis-vinylic position to yield 3,N-dilithio-N-(trialkylsilyl)allylamines under mild conditions. Low temperature (1)H and (7)Li NMR ((1)H NOESY, TOCSY, (1)H/(7)Li HSQC, and DO-NMR) studies on the solution structure of 3,N-dilithio-N-(tert-butyldimethylsilyl)allylamine identified three major aggregates in THF (monomer, dimer and tetramer), but the aggregate structures failed to explain the solvent dependence and regiochemical outcome of the reaction. Low temperature (1)H NMR (NOESY, TOCSY, DO-NMR) studies on the solution structure of N-lithio-N-(tert-butyldimethylsilyl)allylamine in the presence of nBuLi identified amide/nBuLi mixed aggregates in both the ethereal solvent THF (1:1 dimer) and the hydrocarbon solvent toluene (1:3 tetramer). Addition of 2 equiv of THF to toluene solutions induces the formation of the same THF solvated 1:1 dimer as observed in neat THF. NMR evidence suggests that in THF the mixed aggregate has close contact between the olefin and the beta-CH(2) of nBuLi, while in the absence of THF, the allyl chain appears to be pointed away from the nearest nBuLi residues." @default.
• W2065902955 created "2016-06-24" @default.
• W2065902955 creator A5005162937 @default.
• W2065902955 creator A5074276957 @default.
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• W2065902955 date "2005-03-11" @default.
• W2065902955 modified "2023-09-26" @default.
• W2065902955 title "On the Mechanism of THF Catalyzed Vinylic Lithiation of Allylamine Derivatives: Structural Studies Using 2-D and Diffusion-Ordered NMR Spectroscopy" @default.
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• W2065902955 doi "https://doi.org/10.1021/ja0479540" @default.
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• W2065902955 hasPublicationYear "2005" @default.
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