Studies on Stable Free Radicals. IX. Peroxy Acid Oxidation of Hindered Secondary Amines to Nitroxide Radicals

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概要

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• The hindered secondary amines, 2,2,6,6-tetramethyl-4-oxopiperidine (II) and 1,9-diaza-2,2,8,8,10,10-hexamethyl-4-oxo-spiro[5.5]undecane (VI), were oxidized with <I>m</I>-chloroperbenzoic acid, and the corresponding hydroxylamine (III) and <I>N</I>-oxyl-hydroxylamine (VIII), respectively, were isolated. The further oxidation of III and VIII with the peracid afforded the corresponding nitroxide radical IV and IX, in good yields respectively. The stoichiometry of the oxidation reaction of the hydroxylamine III to the nitroxide radical IV was elucidated on the basis of the ESR signal intensities of oxidation products at various molar ratios with the peracid and III. An ESR study of the 1-<SUP>15</SUP><I>N</I>-labelled <I>N</I>-oxyl-hydroxylamine (XII) indicated that there was an intramolecular hydrogen transfer between >N–OH and >N–O · groups in the <I>N</I>-oxyl-hydroxylamines VIII and XII.

• 公益社団法人 日本化学会の論文

著者

• Mori Eiko

  Central Research Laboratories, Sankyo Co., Ltd.

• Toda Toshimasa

  Central Research Laboratories, Sankyo Co., Ltd.

• Murayama Keisuke

  Central Research Laboratories, Sankyo Co, Ltd.

関連論文

• A Novel Cleavage of Carbon-Carbon Triple Bond
• Studies on Stable Free Radicals. XIII. Synthesis and ESR Spectral Properties of Hindered Piperazine N-Oxyls
• Studies on Stable Free Radicals. VI. Synthesis of Substituted 4-Imidazolidinone-1-oxyls
• Studies on Stable Free Radicals. XII. ESR Spectra of 2-t-Butylaminotropone N-Oxyl Radicals
• Studies on Stable Free Radicals. IX. Peroxy Acid Oxidation of Hindered Secondary Amines to Nitroxide Radicals
• A New Route to Nitriles from Thioamides
• Vilsmeier reaction of phenols. I. Synthesis of aryl formates.
• Studies on Stable Free Radicals. VII. The Mechanism for Cyclization Reaction of α-Amino Nitriles with Carbonyl Compounds

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