Abstract
AbstractThe reactions between phthalimide N‐oxyl (PINO) radical and cyclohexene, cyclooctene, and trans‐3‐hexene were carried out. The PINO radical has been in situ generated from its hydroxylimide parent, N‐hydroxyphthalimide (NHPI), applying two approaches: using metallic salts, such as lead tetraacetate and cerium (IV) ammonium nitrate (CAN), and a “metal free” system in which the role of metallic species has been undertaken by antraquinone. In the former case, the strong influence of lead tetraacetate (or CAN) on the NHPI's reactivity, induce two different channels for the reaction pathway, radical and non‐radical, a complex mixture of both saturated and unsaturated diadducts together with the corresponding monoadduct being formed. This behavior will not occur in the case of PINO generation in non‐metallic systems, in this case the reaction pathway proceed exclusively via radical mechanism, with the formation of monoadducts as sole products. Copyright © 2008 John Wiley & Sons, Ltd.
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