Studies of sulfonyl radicals. II. Relative reactivities of ddition reactions of sulfonyl free radicals to vinyl monomers.
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概要
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Addition reactions of various vinyl monomers towards the free methanesulfonyl and arenesulfonyl radicals have been investigated. Relative reactivities of <I>p</I>-methylstyrene (M<SUB>2</SUB>) to styrene (M<SUB>1</SUB>) towards methane- and <I>para</I>-substituted benzenesulfonyl radicals are hardly affected by the kind of sulfonyl radical, suggesting that an unpaired electron of methanesulfonyl and arenesulfonyl radicals is localized mainly on sulfonyl groups. Relative reactivities obtained with vinyl monomers were correlated to Hammett's σ<I><SUB>p</SUB></I> values with ρ<I><SUB>p</SUB></I>=−3.6 and also to Alfrey-Price's <I>e</I> values, indicating that sulfonyl radicals are strongly electrophilic. The highest selectivity of the benzenesulfonyl radical, obtained in the comparison of the selectivity of a number of radicals in addition reactions towards three representative monomers (Table 5), also supports the above conclusion.
- 公益社団法人 日本化学会の論文
著者
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Takahara Yoshiyuki
Chemical Research Center Central Glass Co. Ltd.
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Matsuda Minoru
Chemical Research Institute of Non-aqueous Solutions, Tohoku University
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IINO MASASHI
Chemical Engineering Laboratory, Tokyo Metropolitan University
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Takahara Yoshiyuki
Chemical Research Institute of Non-aqueous Solutions, Tohoku University
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