Abstract
The role of discrete solvent molecules in the reactivity of alkyne cations has been analyzed computationally. Analysis of the possible reaction mechanisms towards competitive cyclization and elimination processes including a molecule of solvent show the crucial role of dichloromethane (DCM) and tetrahydrofuran (THF). In the presence of DCM, a strong intramolecular p‐cation interaction between the electrophilic center and the triple bond favors the [5‐exo‐dig] cyclization route, with no direct participation of the solvent in the reaction path. On the contrary, in the presence of a discrete molecule of THF, a strong solvent–cation interaction via formation of a dative C(+)–O(THF) bond drastically modifies the energy profile, thus promoting the elimination pathway.
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