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Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives and the behavior of o- and p-(hydroxymethyl)benzoates under reductive alkylation conditions



Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives and the behavior of o- and p-(hydroxymethyl)benzoates under reductive alkylation conditions



Journal of Organic Chemistry 78(1): 83-92



Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia-tetrahydrofuran in the presence of tert-butyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of o- and p-(hydroxymethyl)benzoate derivatives results largely in loss of benzylic oxygen substituents. The results are rationalized by computations describing electron density patterns in the putative radical anion intermediate involved in these reactions.

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Accession: 051823819

Download citation: RISBibTeXText

PMID: 23106774

DOI: 10.1021/jo301872n


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