In order to gather direct chemical evidence for the occurrence of protonated cyclopropanes as intermediates in a gas-phase reaction, gaseous cis- and trans-l,2-dimethylcyclopropane were allowed to react with a gaseous Brqnsted acid, the helium tritide ion formed from the decay of molecular tritium. The cis and trans isomers gave the corresponding tritiated compounds retaining the configuration of the original molecules. The lack of any measurable cis-trans isomerization lends strong support to the view that the formation of the tritiated cycloalkanes, following the transfer of a triton from He3H+ to the substrate, proceeds uia a cyclic intermediate, and does not involve the cleavage of the cyclopropane ring. These results corroborate the mechanistic interpretation of earlier experiments concerning the triton transfer from He3H+ to unsubstituted cycloalkanes, and provide unambiguous evidence for the intermediacy of protonated cyclopropanes in a gas-phase reaction.

Reactions of helium tritide ions with gaseous hydrocarbons. V. cis- and trans-1,2-Dimethylcyclopropane. Unambiguous evidence for gaseous protonated cyclopropanes / Cacace, Fulvio; A., Guarino; Speranza, Maurizio. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 93:(1971), pp. 1088-1091.

Reactions of helium tritide ions with gaseous hydrocarbons. V. cis- and trans-1,2-Dimethylcyclopropane. Unambiguous evidence for gaseous protonated cyclopropanes

CACACE, Fulvio;SPERANZA, Maurizio
1971

Abstract

In order to gather direct chemical evidence for the occurrence of protonated cyclopropanes as intermediates in a gas-phase reaction, gaseous cis- and trans-l,2-dimethylcyclopropane were allowed to react with a gaseous Brqnsted acid, the helium tritide ion formed from the decay of molecular tritium. The cis and trans isomers gave the corresponding tritiated compounds retaining the configuration of the original molecules. The lack of any measurable cis-trans isomerization lends strong support to the view that the formation of the tritiated cycloalkanes, following the transfer of a triton from He3H+ to the substrate, proceeds uia a cyclic intermediate, and does not involve the cleavage of the cyclopropane ring. These results corroborate the mechanistic interpretation of earlier experiments concerning the triton transfer from He3H+ to unsubstituted cycloalkanes, and provide unambiguous evidence for the intermediacy of protonated cyclopropanes in a gas-phase reaction.
1971
01 Pubblicazione su rivista::01a Articolo in rivista
Reactions of helium tritide ions with gaseous hydrocarbons. V. cis- and trans-1,2-Dimethylcyclopropane. Unambiguous evidence for gaseous protonated cyclopropanes / Cacace, Fulvio; A., Guarino; Speranza, Maurizio. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 93:(1971), pp. 1088-1091.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/459584
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