Abstract
The reaction of 1-(alk-1-ynyl)-1-halocyclopropanes with alcohols or phenol in KOH/DMSO at 80–100 °C leads to the corresponding alkynylalkoxy- and alkynylphenoxycyclopropanes in up to 80% yield. These reactions proceed through the intermediate formation of conjugated alkynylcyclopropenes capable of the in situ addition of alcohols at the double bond of the cyclopropene fragment. Regio- and stereoselectivity of the process is defined by the nature of substituents in the starting cyclopropanes and the structure of alcohols used.
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Dedicated to Academician B. A. Trofimov in honor of his 70th anniversary.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2078–2085, October, 2008.
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Shavrin, K.N., Gvozdev, V.D. & Nefedov, O.M. Reaction of 1-(alk-1-ynyl)-1-halocyclopropanes with alcohols and phenol in KOH/DMSO as a method for the synthesis of 2-alkoxy-1-alkynyl- and 1-alkynyl-2-phenoxycyclopropanes. Russ Chem Bull 57, 2117–2124 (2008). https://doi.org/10.1007/s11172-008-0287-1
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DOI: https://doi.org/10.1007/s11172-008-0287-1