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

Birch reductive alkylation of methyl <i>m</i>-(hydroxymethyl)­benzoate derivatives, using lithium in ammonia–tetrahydrofuran in the presence of <i>tert</i>-butyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of <i>o</i>- and <i>p</i>-(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

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

Birch reductive alkylation of methyl <i>m</i>-(hydroxymethyl)­benzoate derivatives, using lithium in ammonia–tetrahydrofuran in the presence of <i>tert</i>-butyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of <i>o</i>- and <i>p</i>-(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

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

Birch reductive alkylation of methyl <i>m</i>-(hydroxymethyl)­benzoate derivatives, using lithium in ammonia–tetrahydrofuran in the presence of <i>tert</i>-butyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of <i>o</i>- and <i>p</i>-(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