Abstract
Reactions of 1-alkynyl-1-chlorocyclopropanes with lithium dialkylamides gave previously unknown 1-alkynyl-2-dialkylaminocyclopropanes. 1-(Alk-1-ynyl)-2-diazolylcyclopropanes were obtained by reactions of 1-alkynyl-1-chlorocyclopropanes with diazoles in the presence of KOH in DMSO at 100 °C. These reactions passed through the formation of conjugated alky-nylcyclopropenes and reversible addition of amide anions to them. The regioselectivity and stereoselectivity of these transformations depend on the substituents in the starting chlorocyclopropanes and amines.
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For the preliminary communication, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 388–396, February, 2010.
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Shavrin, K.N., Gvozdev, V.D. & Nefedov, O.M. Synthesis of 1-alkynyl-2-dialkylaminocyclopropanes and 1-alkynyl-2-diazolylcyclopropanes by reactions of 1-alkynyl-1-chlorocyclopropanes with amines and their lithium derivatives. Russ Chem Bull 59, 396–404 (2010). https://doi.org/10.1007/s11172-010-0092-5
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DOI: https://doi.org/10.1007/s11172-010-0092-5