First example of the Mislow-Braverman-Evans rearrangement retaining the sulfur atom on the original carbon |
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| Authors: | Tsuyoshi Satoh Toshifumi Miyagawa |
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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-chloro-2-methylalkenyl p-tolyl sulfoxides with N-lithio 2-piperidone in THF at room temperature resulted in the formation of 1-chloro-2-(hydroxymethyl)alkenyl p-tolyl sulfides in good yields. This reaction is the first example of the Mislow-Braverman-Evans rearrangement retaining the sulfur atom on the original carbon. |
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| Keywords: | Sulfoxide Vinyl sulfoxide Sulfoxide-sulfenate rearrangement Mislow-Braverman-Evans rearrangement Allylic alcohol |
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