Lithiation of 1-alkynyl-1-chlorocyclopropanes and subsequent reactions with electrophilic reagents: synthesis of functionalized alkynyl- and vinylidenecyclopropanes |
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Authors: | Gvozdev V. D. Shavrin K. N. Nefedov O. M. |
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Affiliation: | 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation ; |
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Abstract: | 1-Alkynyl-1-chlorocyclopropanes undergo chlorine-lithium exchange on treatment with BunLi in THF at -40—0 °C. Thus generated organolithium species react with carbon dioxide (dry ice) and acetone to give selectively hitherto unknown 1-alkynylcyclopropanecarboxylic acids and the corresponding alcohols in up to 74% yields. Similar reactions involving methyl chloroformate result in the mixtures of cyclopropylacetylenic and vinylidenecyclopropanic esters, while the use of aliphatic aldehydes as electrophiles provides secondary allenic alcohols in up to 64% yields. |
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