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. 2014 Jul 16;79(16):7520–7531. doi: 10.1021/jo501252p

Table 1. Decay Rates of 1,2,4-Benzotriazine Mustards in Acetonitrile-d6/D2O (1:1) at 50 °C Measured by 1H NMR.

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compd R1 R2 R3 oxidation k (d–1)
17a H2 N(CH2CH2OMs)2 H 1-oxide 0.259 ± 0.060
18a NH2 N(CH2CH2OMs)2 H 1,4-dioxide 0.045 ± 0.002
17b NH2 N(CH2CH2OTs)2 H 1-oxide 0.127 ± 0.014
18b NH2 N(CH2CH2OTs)2 H 1,4-dioxide 0.045 ± 0.002
21 H N(CH2CH2OTs)2 H 1-oxide 0.050 ± 0.004
22 H N(CH2CH2OTs)2 H 1,4-dioxide 0.055 ± 0.006
25 H H N(CH2CH2OTs)2 1-oxide 0.107 ± 0.013
26 H H N(CH2CH2OTs)2 1,4-dioxide 0.106 ± 0.001