A. V. Kalinin, E. A. Shapiro, Yu. V. Tomilov, B. I. Ugrak, A. M. Tsatsakis, O. M. Nefedov, “Selective Non-catalytic Cyclopropanation of Methyl (<i>E</i>)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane”, Mendeleev Commun., 1993, Volume 3, Issue 5,Pages <nobr>190

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Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane

A. V. Kalinin^a, E. A. Shapiro^a, Yu. V. Tomilov^a, B. I. Ugrak^a, A. M. Tsatsakis^b, O. M. Nefedov^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b The School of Health Sciences, University of Crete, Iraklion, Crete, Greece

Abstract: 1,3-Dipolar cycloaddition of diazomethane to methyl (E)-pent-3-en-1-yn-3-ylcarboxylates proceeds selectively with participation of only the double bond, resulting in unstable methyl 3-alkynylpyrazolinylcarboxylates, thermolysis of which leads to methyl 1-alkynylcyclopropanecarboxylates and 4-methylpent-3-en-1-yn-3-ylcarboxylates.

Language: English

DOI: 10.1070/MC1993v003n05ABEH000281