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. 2018 Oct 9;3(10):12868–12877. doi: 10.1021/acsomega.8b02320

Table 3. Control Reactions and Mechanistic Experiments.

graphic file with name ao-2018-02320j_0009.jpg

entry deviation from standard conditions % yield 3a
1 none 90
2 0.4 equiv (NH4)2S2O8 90
3 0.4 equiv (NH4)2S2O8, reaction in darkb 32
4 0.4 equiv (NH4)2S2O8, no erythrosine B 56
5 no erythrosine B, no (NH4)2S2O8 14
6 anaerobic conditionsc 68
7 anaerobic conditionsc, no (NH4)2S2O8 7
8 no (NH4)2S2O8, 1 equiv BHT added 0
9 no (NH4)2S2O8, 1 equiv TEMPO added 0
a

GC yields calculated using adamantane as the internal standard.

b

Reaction vessel was covered in an aluminum foil, and the reaction was carried out in a laboratory with the lights turned off.

c

Solvent was degassed, and the reaction was conducted under argon.