The first example of magnesium carbenoid 1,3-CH insertion reaction: a novel method for synthesis of cyclopropanes from 1-chloroalkyl phenyl sulfoxides in high yields |
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Authors: | Tsuyoshi Satoh Jun Musashi Atsushi Kondo |
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Affiliation: | Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan |
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Abstract: | Treatment of 1-chloroalkyl phenyl sulfoxides having a geminal methyl group or a geminal benzyl group at the 2-position in THF at −78 °C with isopropylmagnesium chloride gave magnesium carbenoids. Carbenoid 1,3-CH insertion reaction of the magnesium carbenoids took place instantaneously to afford cyclopropanes in high to quantitative yields. |
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Keywords: | Cyclopropane Sulfoxide Sulfoxide-magnesium exchange Magnesium carbenoid C-H insertion |
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