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8544221237
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note
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The transformation of 13 into 1 can be achieved by the reaction of 13 with 1.5 equiv of benzoyl peroxide in benzene under reflux. In our hands, superior yields were always obtained by the stepwise transformation 13 → 15 → 1, especially in the preparation of ebselen (1: R = Ph) where solubility problems are encountered.
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36
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8544229273
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note
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A reviewer suggested that tert-butyl peroxide may be undergoing induced decomposition at 120 °C, thus acting as a more effective scavenger of methyl radicals at higher concentrations.
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37
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8544237884
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note
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TLC analysis indicated that the starting material was consumed after 16 h. Prolonged exposure to tert-butyl peroxide at 120 °C resulted in a significantly darker reaction mixture and diminished yields of ebselen (1, R = Ph).
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42
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8544272625
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note
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Heating concentrated tert-butyl peroxide at 120 °C is potentially hazardous and should never be attempted on a large scale. This experiment was carried our behind a protective (safety) shield.
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