Issue 42, 2012

Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes

Abstract

The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoretically investigated using DFT methods in order to explain the reactivity and regioselectivity observed.

Graphical abstract: Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes

Supplementary files

Article information

Article type
Paper
Submitted
24 Jul 2012
Accepted
11 Sep 2012
First published
12 Sep 2012

Org. Biomol. Chem., 2012,10, 8434-8444

Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes

G. Bentabed-Ababsa, S. Hamza-Reguig, A. Derdour, L. R. Domingo, J. A. Sáez, T. Roisnel, V. Dorcet, E. Nassar and F. Mongin, Org. Biomol. Chem., 2012, 10, 8434 DOI: 10.1039/C2OB26442K

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