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Cycloaddition versus amidation in reactions of 2-amino-2-oxoethyl-phenanthrolinium ylides to activated alkynes and alkenes
Authors:Cristina M. Al Matarneh  Catalina I. Ciobanu  Mircea O. Apostu  Ionel I. Mangalagiu  Ramona Danac
Affiliation:1. Department of Chemistry, Faculty of Chemistry, “Al. I. Cuza” University of Iasi, 11 Carol I, Iasi 700506, Romania;2. Research Department, Faculty of Chemistry, “Al. I. Cuza” University of Iasi, 11 Carol I, Iasi 700506, Romania
Abstract:A comparative study regarding cycloaddition versus amidation reactions of 2-amino-2-oxoethyl-phenanthrolinium ylides to activated alkynes and alkenes is presented. The reaction pathway is different, depending on dipolarophile (with triple or double bond) and ylide structures. The monoenamidation reaction proved to be stereoselective leading to a Z-stereochemistry on the acrylate double bond. The structures of all newly synthesized compounds have been proved by spectral analysis (NMR and IR) and in some cases by X-ray diffraction.
Keywords:3 + 2 Cycloaddition  Phenanthroline  Pyrrolophenanthroline
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