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Cycloaddition versus amidation in reactions of 2-amino-2-oxoethyl-phenanthrolinium ylides to activated alkynes and alkenes |
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| Authors: | Cristina M Al Matarneh Catalina I Ciobanu Mircea O Apostu Ionel I Mangalagiu Ramona Danac |
| Institution: | 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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