Halogenation with N-halo-2-oxazolidinones. The chain-carrying N-centered radicals.
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概要
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Selectivities in halogenation of 2,3-dimethylbutane, 1-chlorobutane and substituted toluenes with <I>N</I>-chloro-or <I>N</I>-bromo derivatives of 4,4-dimethyl-2-oxazolidinone (NXDMO), 2-oxazolidinone (NXO), and succinimide (NXS) were examined. In the presence of olefin, halogenation of the substituted butane by these <I>N</I>-halo reagents were found to proceed involving hydrogen abstraction by the <I>N</I>-centered radicals, since chlorination by the <I>N</I>-chloro reagents and bromination by the corresponding <I>N</I>-bromo reagents showed the same selectivities. The relative reactivity of a <I>t</I>-C-H bond compared with a <I>prim</I>-C-H bond RS<SUB>p</SUB><SUP>t</SUP> markedly depends on the structure of the <I>N</I>-radical, being 200, 70, and 11 at 80 °C toward the radicals derived from NXDMO, NXO, and NXS, respectively. Reaction constant ρ of hydrogen abstraction from the toluenes by the <I>N</I>-radical from NXDMO was −1.0 at 130 °C.
- 公益社団法人 日本化学会の論文
著者
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Kosugi Masanori
Department Of Chemistry Faculty Of Engineering Gunma University
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Watanuki Toshiro
Department of Applied Chemistry, Faculty of Technology, Gunma University
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Migita Toshihiko
Department of Chemistry, Faculty of Engineering, Gunma University
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Suzuki Mikio
Department of Applied Chemistry, Faculty of Technology, Gunma University
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Nakayama Mitsumasa
Department of Applied Chemistry, Faculty of Technology, Gunma University
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