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10544221539
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note
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Filtration through a short plug of neutral alumina enabled us to characterize 2e. In contrast, the corresponding diorganostannane 3e could be purified by rapid chromatography on silica gel, which suggests the greater instability of 2e is attributed to the presence of the double bond enabling the formation of a conjugated diene.
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note
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See Supporting Information. Quenching the organolithium with AcOD gave the corresponding monodeuterated homoallylic alcohol with ≥95% deuterium incorporation.
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Separation of each of these nonpolar compounds and hexabutylditin by chromatography on silica gel is not readily accomplished, therefore the yields reported have not been optimized.
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