eng Science and Education Publishing World Journal of Organic Chemistry 2372-2169 2017-07-06 5 1 6 10 10.12691/wjoc-5-1-2 WJOC2017512 article Promi Rahman 1 Amy Glanzer 1 Jaffarguriqbal Singh 1 Nanette M. Wachter 1 Jonathan Rhoad 2 Richard W. Denton rdenton@barnard.edu 3 Department of Chemistry, Hofstra University, Hempstead, United States of America .Department of Chemistry, Missouri Western State University, St. Joseph, United States of America Department of Chemistry, Barnard College, New York, United States of America 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. http://pubs.sciepub.com/wjoc/5/1/2/wjoc-5-1-2.pdf 1,3-Dipolar cyclization isoxazole solvent effect regioselectivity density functional theory calculations