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. Author manuscript; available in PMC: 2019 May 9.
Published in final edited form as: J Am Chem Soc. 2018 Apr 25;140(18):5969–5975. doi: 10.1021/jacs.8b02535

Table 3.

Attempted Atropisomerism of Gonytolide Dimers

graphic file with name nihms961096u4.jpg
entry X conditionsa results
1 H 0.1 equiv. FeCl3, DCE/HFIP 1:1, rt No reaction
2 Br 0.1 equiv. FeCl3, 1.5 equiv. t-BuOOt-Bu, DCE/HFIP 1:1, rt No reaction
3 H 0.1 equiv. 9-mesityl-10-methylacridinium tetra-fluoroborate, CH3CN, 427 nm, rt Complete decomposition
4 Br 0.1 equiv. 9-mesityl-10-methylacridinium tetra-fluoroborate, CH3CN, 427 nm, rt No reaction
5 Br 0.5 equiv. (NH4)2Ce(NO3)6, CH3CN/H2O 1:1, rt Decomposition
6 Br 0.5 equiv. VOF3, TFA/TFAA 20:1, rt Complete decomposition
a

Reaction conducted for 12 h unless specified otherwise.