Comparison of the Nucleophilicities of Alkynes and Alkenes. Quantitative Determination of the Nucleophilicities of Alkynes toward Carbenium Ions

Mayr, Herbert; Gonzalez, Jose L. und Lüdtke, Kerstin (1994): Comparison of the Nucleophilicities of Alkynes and Alkenes. Quantitative Determination of the Nucleophilicities of Alkynes toward Carbenium Ions. In: Chemische Berichte, Bd. 127, Nr. 3: S. 525-531

Abstract

Relative reactivities of alkenes and alkynes toward diarylmethyl cations have been determined by direct rate measurements and by competition experiments in dichloromethane. At -70°C alkynes are found to be one to two orders of magnitude less reactive than analogously substituted alkenes (e.g. phenylacetylene/styrene), but the reactivity difference reduces strongly as the temperature is raised. The stereochemistry of the vinyl chlorides produced by addition of benzhydryl chlorides to alkynes is characterized.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• Signatur: Chem. 26 h-127,1/4