The first example of 2,2-dilithiocyanocyclopropanes: generation from 2-bromo-2-sulfinylcyanocyclopropanes with tert-butyllithium, property, and a synthesis of fully substituted cyanocyclopropanes |
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Authors: | Iori Fukushima |
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Institution: | Department of Chemistry, Faculty of Science, Tokyo University of Science, Ichigaya-funagawara-machi 12, Shinjuku-ku, Tokyo 162-0826, Japan |
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Abstract: | 2,2-Dilithiocyanocyclopropanes were easily generated from 2-bromo-2-(p-tolylsulfinyl)cyanocyclopropanes with tert-butyllithium in toluene at −78 °C through concomitant sulfoxide-lithium and bromine-lithium exchange reactions. The gem-dianions were found to be stable at −78 °C for at least 30 min. Reaction of the gem-dianions with electrophiles gave fully substituted cyanocyclopropanes in moderate yields. |
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Keywords: | Geminal dianion 1 1-Dilithiocyclopropane Cyanocyclopropane Sulfoxide-lithium exchange Bromine-lithium exchange |
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