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. Author manuscript; available in PMC: 2023 Jan 21.
Published in final edited form as: J Org Chem. 2022 Jan 6;87(2):1398–1420. doi: 10.1021/acs.joc.1c02700

Table 2.

Optimization of the 6-electron Birch reduction of 88 with avoidance of formation of diol 90

graphic file with name nihms-1824212-t0027.jpg
Entn H+ source Co-solvent Co-solvent:
NH3 ratio		 Prodoct Inverse
addition		  % Arene
redutcion
1 MeOH THF 1:4 90 no 40%
2 MeOH THF 1:2 90 no 75%
3 t-BuOH THF 1:5 89 no 46%
4 t-BuOH THF 1:1 89 yes 89%
5 t-BuOH dioxane 1:3 89 yes 88%
6 t-BuOH DME 1:3 89 yes >95%
7 s-BuOH DME 1:3 89 yes 86%