Skip to main content
. 2012 Dec 21;113(1):119–191. doi: 10.1021/cr300177k

Table 3. 2,5-Dimethylphenacyl (8, DMP) Photoremovable Group.

leaving group, X (protected species) solvent quantum yield, Φ chemical yield of HX release (%) kapp/s–1a
Cl benzene 0.1156a (0.12)54a   4.4 × 1061
methanol 0.7656a (0.78)54a   4.4 × 1061
OC(=O)R (carboxylic acids) benzene 0.18–0.2554b,57b 85–9554b ∼257b
methanol 0.09–0.1457b 9254b 4.5 × 1057b
OP(=O)(OR)2 (phosphates) benzene 0.0954a   ∼254a
methanol 0.7154a 9454a 5 × 1054a
OS(=O)2R (sulfonic acids) benzene 0.16–0.1954a    
methanol 0.6854a 90–9354a 4 × 1054a
OC(=O)OR (alcohols) cyclohexane 0.36–0.5158 >7058 b
methanol 0.09–0.2058   b
OC(=O)NR2 (amines) cyclohexane 0.054–0.08959   b
acetonitrile 0.035–0.07059 9759 b
methanol 0.027–0.06159   b
a

Appearance rate constant of the leaving group, calculated as kapp = 1/τenol.

b

Slow, presumably <1 ms–1.