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- W4307340147 endingPage "14229" @default.
- W4307340147 startingPage "14223" @default.
- W4307340147 abstract "The preparation, structure, physical properties, and reactivities of sodium isopropyl(trimethylsilyl)amide (NaPTA) are described. The solubilities at room temperature range from n-heptane (0.55 M), n-hexane (0.60 M), toluene (0.65 M), MTBE (1.7 M), Et3N (3.2 M), and THF (>6.0 M). The half-life to destruction in neat THF is >1 year at 25 °C and 7 days at 70 °C, which compares favorably to 2.5 months and 1.5 days, respectively, for LDA in neat THF. This study focuses on NaPTA in THF. 29Si NMR spectroscopy shows exclusively a mixture of cis and trans stereoisomeric dimers in 0.10-12 M THF in hexane. Density functional theory (DFT) computations suggest that the pKb is intermediate between dimeric sodium diisopropylamide (NaDA) and dimeric sodium hexamethyldisilazide (NaHMDS). Metalations of arenes, epoxides, ketones, hydrazones, alkenes, and alkyl halides show higher reactivities than LDA (kNaPTA/LDA = 1-30). While the rates of arene metalation are high, the lower pKb of NaPTA limits the substrates. Metalation of pseudoephedrate-based carboxamides to form disodiated Myers enolates solves several challenging technical problems." @default.
- W4307340147 created "2022-10-31" @default.
- W4307340147 creator A5008735740 @default.
- W4307340147 creator A5039594674 @default.
- W4307340147 creator A5044561698 @default.
- W4307340147 creator A5074374544 @default.
- W4307340147 creator A5080756186 @default.
- W4307340147 date "2022-10-25" @default.
- W4307340147 modified "2023-10-14" @default.
- W4307340147 title "Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic" @default.
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- W4307340147 doi "https://doi.org/10.1021/acs.joc.2c01745" @default.
- W4307340147 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/36282953" @default.
- W4307340147 hasPublicationYear "2022" @default.