Substituent Effect of Dipole and Dipolarophile in the Reaction of Nitrones with <I>N</I>-(Substituted phenyl)maleimides
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概要
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The reactions of <I>C</I>-(<I>p</I>-substituted phenyl)-<I>N</I>-(<I>p</I>-substituted phenyl) nitrones with <I>N</I>-(<I>p</I>-substituted phenyl)maleimides were carried out in THF to give both <I>trans</I>- and <I>cis</I>-isoxazolidines. The formation ratios of <I>trans</I>- to <I>cis</I>-isoxazolidines (<I>I</I><SUB>T</SUB>⁄<I>I</I><SUB>c</SUB>) were determined by the NMR spectra of the cycloadduct mixtures. Though the values of <I>I</I><SUB>T</SUB>⁄<I>I</I><SUB>c</SUB> varied with the electronic characters of the substituents, R<SUB>1</SUB>, R<SUB>2</SUB>, and R<SUB>3</SUB>, they were always found to be larger than unity.
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