Photochemical Rearrangement of Chlorinated Dibenzo-p-dioxins. Regioselective Carbon-Oxygen Bond Homolysis from the Singlet Excited State, and Carbon-Chlorine Bond Homolysis from the Triplet Excited State
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UV light irradiation of 1-chloro-, 2-chloro-, 1,2-dichloro-, 2,3-dichloro-, and 2,7-dichlorodibenzo-<I>p</I>-dioxin in methanol leads to regioselective homolysis of carbon–oxygen bond from the singlet excited state to undergo rearrangement into chlorinated 2,2′-biphenols. On the contrary, reaction from the triplet excited state of chlorinated dioxins results in selective formation of dechlorinated congeners without altering the dioxin skeleton.
- Chemistry Letters
Chemistry Letters 35(4), 348-349, 2006-04-05
The Chemical Society of Japan