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

SJ Fretz, CM Hadad, DJ Hart, S Vyas…

Index: Fretz, Samuel J.; Hadad, Christopher M.; Hart, David J.; Vyas, Shubham; Yang, Dexi Journal of Organic Chemistry, 2013 , vol. 78, # 1 p. 83 - 92

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Citation Number: 4

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 ...