Phosphorus, Sulfur and Silicon and the Related Elements p. 363 - 376 (2006)
Update date:2022-08-04
Topics:
Haikou, Maria N.
Ioannou, Panayiotis V.
Triaryl trithioarsenites, (ArS)3As, are oxidized by air to As2O3 and ArSSAr. In two cases the parent "thiol" (pyrid-2-thione and 1-hydroxypyrid-2-thione) is coproduced. The oxidation, in nonprotic solvents, is favored by electron-withdrawing groups at the para position of the phenyl group. The products obtained in nonprotic solvents were rationalized by assuming that the binding of the triplet dioxygen to arsenic(III) gives a triplet diradical, (ArS)3As-O-O, or an arsenadioxirane, (ArS)3As(O2), intermediate, which decomposes after nucleophilic attack by another (ArS)3As molecule. In protic solvents a zwitterion, (ArS)3As+-O-O-, and in the presence of moisture a hydroperoxy arsenic(V) compound, (ArS) 3As(OH)-O-OH, may be intermediates in the air oxidation of some aromatic trithioarsenites. These data tend to indicate that arsenic(III) bound to suitable groups can directly bind dioxygen, a property which may have implications in chemotherapy and carcinogenesis. Copyright Taylor & Francis Group, LLC.
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