Collect. Czech. Chem. Commun. 2004, 69, 426-434

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


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.