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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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1384–1390, July, 2019.
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Gvozdev, V.D., Shavrin, K.N. & Nefedov, O.M. Lithiation of 1-alkynyl-1-chlorocyclopropanes and subsequent reactions with electrophilic reagents: synthesis of functionalized alkynyl- and vinylidenecyclopropanes. Russ Chem Bull 68, 1384–1390 (2019). https://doi.org/10.1007/s11172-019-2566-4
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DOI: https://doi.org/10.1007/s11172-019-2566-4