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Caplan, J. F., Zheng, R., Blanchard, J. S. and Vederas, J C., Vinylogous amide analogues of diaminopimelic acid (DAP) as inhibitors of enzymes involved in bacterial lysine biosynthesis Organic lett., 2 (24), 3857-3860, 2000.

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Article

Solvent Effects on the [3+2] Cycloaddition of 2-Furfural Oxime and Ethyl Propiolate: Unexpected Change in Regioselectivity

1Department of Chemistry, Hofstra University, Hempstead, United States of America

2Department of Chemistry, Missouri Western State University, St. Joseph, United States of America

3Department of Chemistry, Barnard College, New York, United States of America


World Journal of Organic Chemistry. 2017, Vol. 5 No. 1, 6-10
DOI: 10.12691/wjoc-5-1-2
Copyright © 2017 Science and Education Publishing

Cite this paper:
Promi Rahman, Amy Glanzer, Jaffarguriqbal Singh, Nanette M. Wachter, Jonathan Rhoad, Richard W. Denton. Solvent Effects on the [3+2] Cycloaddition of 2-Furfural Oxime and Ethyl Propiolate: Unexpected Change in Regioselectivity. World Journal of Organic Chemistry. 2017; 5(1):6-10. doi: 10.12691/wjoc-5-1-2.

Correspondence to: Richard  W. Denton, Department of Chemistry, Barnard College, New York, United States of America. Email: rdenton@barnard.edu

Abstract

The effect of solvents on the 1,3-dipolar cyclization reaction between ethyl propiolate and 2-furfuryl nitrile oxide was studied in various organic solvents. As expected, the major product was ethyl-3-(2-furanyl)-5-carboxylate. The relative ratio of the 3,5- to 3,4- disubstituted isoxazoles in dichloromethane, toluene, ethanol and dimethyl sulfoxide were 3.4, 2.0, 1.9 and 1.5 respectively. Experimental regioselectivity was found to be dissimilar to density functional theory predictions.

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