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84920311048
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note
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Spectral data are consistent with the following structure: equation presented
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29
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34
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84920311047
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note
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2O and 20-30% yield in THF at -100 °C. The poor results from these reactions may be due to the electron-withdrawing effect of the aromatic nitro group, as it is capable of activating the adjacent methyl group to nucleophilic substitution. Methyl nucleophiles, therefore, attack the aromatic methyl, resulting in demethylation of the benzenic ring.
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