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A variety of vinylic alkoxyamines derived from propargyl alcohols and 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) were synthesized in good yields under copper-catalyzed aerobic conditions. A reaction mechanism was proposed, involving the isomerization of propargyl radicals to allenic radicals, and related mechanistic studies were performed. The kinetic isotope effect on the propargyl C-H bond cleavage (α-deprotonation) reaction was observed (kH/kD = 3.76).
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Kang et al. (2014) studied this question.
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