Studies on Stable Free Radicals. V Reactivity of a Stable Free Radical, 2,2,6,6-Tetramethyl-4-oxopiperidine-1-oxyl
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概要
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A stable <I>N</I>-oxyl radical, 2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl (I), afforded 1-hydroxy-2,2,6,6-tetramethyl-3-(2,2,6,6-tetramethyl-4-oxopiperidinoxy)-4-oxopiperidine (IX) by hydrogen-abstraction followed by the coupling reaction of the <I>N</I>-oxyl radical I with the <I>C</I> radical III derived from I. The product IX was characterized as the monoacetate (X), monobenzoate (XI), urethane (XII), semicarbazone (XIII), triol (XIV), triacetate (XV), and a new <I>N</I>-oxyl radical (XVI). It has been confirmed that i) the extremely stable <I>N</I>-oxyl radical abstracts the α-methylene-hydrogen of the ketone which affords a thermodynamically stable conjugated ketone, ii) radical I acts as a scavenger toward a <I>C</I>-radical intermediate and iii) the decomposition of radical I proceeds <I>via</I> the <I>C</I>-radical to give phorone (V).
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