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Nitroxyl radicals (nitroxides) with unpaired electron are widely used as antioxidants, contrast agents, and spin probes. Although piperidine nitroxyl radicals have many applications, these are mainly tetramethylpiperidine compounds, and only a few reports consider the substitution of N–O surround as a reaction site, such as 2,2,6,6-tetrasubstituted piperidine nitroxyl radicals. Our results revealed that the 2,6-position of the 2,2,6,6-tetramethylpiperidin-4-one compound was substituted by cyclohexyl groups to produce 2,2,6,6-tetrasubstituted piperidin-4-one derivatives under mild reaction conditions. An interesting result was obtained by using 15N-labeled NH4Cl instead of 14NH4Cl: it gave 15N-labeled 2,2,6,6-tetrasubstituted piperidin-4-one-1-oxyls with a high 15N content. In conclusion, the new method for the synthesis of nitroxyl radicals readily yields 2,2,6,6-tetrasubstituted piperidin-4-one under mild conditions. |
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