Synthesis of cis-aryl cyclopropyl sulfones.
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概要
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Some new <I>cis</I>-1-(arylsulfonyl)-2-phenylcyclopropanes have been synthesized by the addition of arylthiocarbenes to styrene in presence of excess potassium <I>t</I>-butoxide at low temperatures. The (arylthio)cyclopropanes thus obtained are subsequently oxidized with 30% hydrogen peroxide in acetic acid to corresponding sulfones. The IR and PMR spectra of all these compounds were recorded. Their IR spectra displayed bands in the region 1033–1008 cm<SUP>−1</SUP> which are considered to be the most characteristic of the cyclopropane ring. They have also exhibited bands in the region 850–820 cm<SUP>−1</SUP> characteristic of <I>cis</I>-configuration. The PMR spectra gave complex multiplets in the region 1.4–3.1 ppm. A study of these chemical shifts for ring protons and other substituents reveals that all the substituents tend to cause protons <I>cis</I>-to them to appear at higher fields than those <I>trans</I>-to them. Thus the differences of the chemical shifts can be used as a criterion to distinguish between <I>cis</I>-and <I>trans</I>-1-(arylsulfonyl)-2-phenylcyclopropanes.
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著者
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Reddy D.
Department of Chemistry, Post-Graduate Centre, Sri Venkateswara University
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Reddy D.
Department of Chemistry, Sri Venkateswara University
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Balaji T.
Department of Chemistry, Sri Venkateswara University