World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: Editor-in-chief: Subrata Shaw
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World Journal of Organic Chemistry. 2017, 5(1), 6-10
DOI: 10.12691/wjoc-5-1-2
Open AccessArticle

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

Promi Rahman1, Amy Glanzer1, Jaffarguriqbal Singh1, Nanette M. Wachter1, Jonathan Rhoad2 and Richard W. Denton3,

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

Pub. Date: July 06, 2017

Cite this paper:
Promi Rahman, Amy Glanzer, Jaffarguriqbal Singh, Nanette M. Wachter, Jonathan Rhoad and 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


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.

13-Dipolar cyclization isoxazole solvent effect regioselectivity density functional theory calculations

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