Modeling of Solvolysis Reaction Mechanism for Cation-Olefin Cyclizations

Authors

  • Guillaume Bollot
  • Céline C.J. Fouillet
  • Jiri Mareda

DOI:

https://doi.org/10.2533/000942905777676740

Keywords:

Ab initio, Carbocations, Cation-olefin cyclizations, Molecular modeling, Solvent effects

Abstract

We report on a computational study of cation-olefin cyclization mechanism under solvolytic conditions. The combined explicit-continuum solvent model aimed at providing a complete estimate of media effects is used to investigate the nature, stability, and conformational behavior of cationic species involved in the reaction. The comparison between the explicit-continuum and leaving group models is also provided. Our study of reactionpath ways shows that protonated cyclopropane is the key intermediate on the potential energy surface of cation-olefin cyclizations.

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Published

2005-03-01