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Impurities in aged stock solutions of n-BuLi, such as LiOH and n-BuOLi, may cause decomposition of 1a or may alter the aggregation properties of the nucleophile. TMEDA seemed to abrogate this effect.
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50
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3Si group occurred during purification.
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3. See Supporting Information for details.
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63
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33646581588
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note
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+ = 261.1); however, the yield was quite low, and we could not isolate the desired product in acceptable purity. In the latter case, the reaction resulted in the decomposition of triflate 1a, and a significant amount of ethyl isobutyrate was recovered.
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64
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33646541583
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note
-
A further mechanistic discussion can be found in our earlier paper; see ref 19.
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75
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note
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1H NMR data consistent with metastable intermediate C1′ were routinely observed during spectroscopic analysis of the crude reaction mixtures.
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