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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
Authors:Tsuyoshi Satoh  Jun Musashi  Atsushi Kondo
Affiliation:Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
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.
Keywords:Cyclopropane   Sulfoxide   Sulfoxide-magnesium exchange   Magnesium carbenoid   C-H insertion
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