Birch Reductive Alkylation of Methyl m-(Hydroxymethyl)benzoate Derivatives and the Behavior of o- and p-(Hydroxymethyl)benzoates under Reductive Alkylation Conditions

作者：Fretz Samuel J; Hadad Christopher M; Hart David J^*; Vyas Shubham; Yang Dexi

来源：Journal of Organic Chemistry, 2013, 78(1): 83-92.

DOI：10.1021/jo301872n

Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia tetrahydrofuran in the presence of tertbutyl 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.

• 出版日期2013-1-4