Homolytic Chlorination of Aliphatic Compounds. IV. Chlorination of Chloroalkanes by <I>t</I>-Butyl Hypochlorite
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概要
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Chlorination of chloroalkanes by <I>t</I>-butyl hypochlorite was investigated by means of competitive experiment. Relative reactivities thus obtained were compared with those toward hydrogen abstraction by <I>t</I>-butoxy radicals derived from other sources. From the results it was concluded that a main chain carrier of this chlorination was a <I>t</I>-butoxy radical. Structure-reactivity relationships in <I>t</I>-butyl hypochlorite chlorination were also investigated. Linear free energy relationship was found to exist between the reactivities of methyl hydrogen of CH<SUB>3</SUB>-X and Taft's σ<SUP>*</SUP> constants for the substituent X,ρ<SUP>*</SUP>=−0.69. α-Chlorine substituents were found always to enhance the rate of hydrogen abstraction of this position. Resonance effects of a-chlorine substituent is considered to be more important than in photochlorination with chlorine.
- 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, Gunma University
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Kosugi Masanori
Department Of Chemistry Faculty Of Engineering Gunma University
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Takeuchi Kohji
Department Of Life Science Faculty Of Science Himeji Institute Of Technology
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Migita Toshihiko
Department of Chemistry, Gunma University
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Migita Toshihiko
Department of Chemistry, Faculty of Engineering, Gunma University
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