Selective Formations of Several Carboxylic Acids by Carbonylation in the SbCl<SUB>5</SUB>–Liquid Sulfur Dioxide System

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概要

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• The carbonylations of <I>cis</I>- and <I>trans</I>-4-<I>t</I>-butyl-1-methylcyclohexanols, <I>exo</I>- and <I>endo</I>-2-methyl-2-norbornanols and <I>exo</I>- and <I>endo</I>-2-norbornanols were carried out in SbCl<SUB>5</SUB>–liq.SO<SUB>2</SUB> at −70°. From both the <I>cis</I>- and <I>trans</I>-4-<I>t</I>-butyl-1-methyl-cyclohexanols, <I>cis</I>-4-<I>t</I>-butyl-1-methylcyclohexanecarboxylic acid was formed exclusively in an excellent yield (over 90%). Both <I>exo</I>- and <I>endo</I>-2-methyl-2-norbornanols gave only <I>endo</I>-2-methyl-<I>exo</I>-2-norbornylcarboxylic acid in a high yield. The reason for the stereoselectivity of the reactions was discussed.

• 公益社団法人 日本化学会の論文

著者

• Tokura Niichiro

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Nojima Masatomo

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Yoshimura Masakatsu

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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