Collect. Czech. Chem. Commun.
2004, 69, 426-434
https://doi.org/10.1135/cccc20040426
1,3-Dipolar Cycloaddition Reactions of 4-Halophenylphthalazinium Ylides to Activated Alkenes and Alkynes
Maria C. Caprosu, Gheorghita N. Zbancioc, Costel C. Moldoveanu and Ionel I. Mangalagiu*
Organic Chemistry Department, Al. I. Cuza University, B-dul Carol-11, Iasi-6600, Romania
Abstract
For the first time in the benzodiazinium ylide series cycloaddition of (4-halophenyl) substituted ylides to activated alkenes and alkynes was studied. The ability of these ylides to react with acrylonitrile, N-phenylmaleimide, ethyl propiolate and dimethyl acetylenedicarboxylate was investigated. The stereochemistry and regiochemistry involved in these reactions are also discussed. Two new salts and ten new azabicyclic compounds have been obtained.
Keywords: 1,3-Dipolar cycloadditions; Ylides; Alkenes; Alkynes; Stereoselective synthesis; Azabicyclic; Phthalazine.
References: 13 live references.
