title: Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives and the behavior of o- and p-(hydroxymethyl)benzoates under reductive alkylation conditions.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States.
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Fretz
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Hadad
authors.forename: David J
authors.initials: DJ
authors.lastname: Hart
authors.forename: Shubham
authors.initials: S
authors.lastname: Vyas
authors.forename: Dexi
authors.initials: D
authors.lastname: Yang