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. Author manuscript; available in PMC: 2018 Oct 20.
Published in final edited form as: J Org Chem. 2017 Oct 10;82(20):11072–11083. doi: 10.1021/acs.joc.7b02017

Table 2.

Product Yields from Photolysis of Radical Cation Precursor NMe-6

% yielda

conditionsb NMe-13 NMe-14 27 28 NMe-16 NMe-17 NMe-T NMe-6 mass balance
H2O 15.5 ± 1.7 7.7 ± 1.1 7.2 ± 0.2 4.8 ± 1.1 5.4 ± 0.5 3.5 ± 0.3 33.4 ± 0.3 7.3 ± 6.5 84.8 ± 3.0
BMEc 3.8 ± 2.6 13.2 ± 3.5 2.6 ± 0.5 1.8 ± 0.6 1.6 ± 0.4 1.5 ± 0.2 71.4 ± 1.1 6.5 ± 6.7 102.4 ± 7.2
BMEd(after hν) 4.4 ± 3.7 17.8 ± 0.6 8.4 ± 0.8 5.3 ± 0.6 7.0 ± 0.6 4.5 ± 0.6 33.4 ± 0.3 2.8 ± 0.4 83.7 ± 1.4
pH 5.0 (Chelex) 9.0 ± 0.1 6.5 ± 0.3 3.1 ± 0.2 6.1 ± 0.1 3.8 ± 0.1 3.2 ± 0.2 28.1 ± 0.1 7.6 ± 6.9 67.3 ± 6.3
pH 5.0 9.5 ± 0.4 6.8 ± 0.1 3.3 ± 0.1 6.4 ± 0.2 3.9 ± 0.1 3.6 ± 0.4 28.6 ± 0.5 7.4 ± 7.1 69.3 ± 6.0
pH 7.2 20.8 ± 1.9 10.6 ± 1.1 3.3 ± 0.4 3.0 ± 0.5 4.3 ± 0.3 5.9 ± 0.1 32.5 ± 0.4 8.1 ± 7.0 88.5 ± 5.8
pH 8.0 18.0 ± 0.3 11.2 ± 0.4 3.4 ± 0.3 2.8 ± 0.2 2.4 ± 0.1 6.2 ± 0.5 32.7 ± 0.2 8.8 ± 7.7 85.5 ± 7.0
a

Yields and mass balances are the average ± standard deviation of at least 3 measurements.

b

All experiments were carried out in a 1:1 (v/v) mixture of CH3CN and the solvent listed.

c

[BME] = 10 mM.

d

[BME] = 100 mM at 37 °C for 1 h.