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Mayr, Herbert; Gonzalez, Jose L.; Lüdtke, Kerstin (1994): Comparison of the Nucleophilicities of Alkynes and Alkenes. Quantitative Determination of the Nucleophilicities of Alkynes toward Carbenium Ions. In: Chemische Berichte, Vol. 127, No. 3: pp. 525-531


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.