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Bond Memory in Dynamically Determined Stereoselectivity.

Vladislav A Roytman1, Shengfei Jin2, Vu T Nguyen2

  • 1Department of Chemistry , Texas A&M University , P.O. Box 30012, College Station , Texas 77842 , United States.

Journal of the American Chemical Society
|December 20, 2019
PubMed
Summary
This summary is machine-generated.

Carboborative ring contraction of cyclohexenes shows unusual selectivity, forming both inversion and retention products from a single transition state. This selectivity arises from the distinct behavior of new versus old bonds during the reaction dynamics.

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Area of Science:

  • Organic Chemistry
  • Reaction Dynamics
  • Stereochemistry

Background:

  • Carboboration reactions are crucial for synthesizing carbocyclic compounds.
  • Cyclohexene derivatives undergo ring contraction reactions with unique mechanistic pathways.
  • Understanding stereoselectivity in concerted reactions is key to controlling product formation.

Purpose of the Study:

  • To investigate the abnormal selectivity observed in the carboborative ring contraction of cyclohexenes.
  • To elucidate the dynamic origins of stereochemical outcomes in this reaction.
  • To correlate computational trajectories with experimental product ratios.

Main Methods:

  • Computational modeling of reaction dynamics using dynamic trajectories.
  • Analysis of transition state structures and energy profiles.
  • Comparison of calculated product distributions with experimental data.

Main Results:

  • The carboborative ring contraction yields predominantly inversion products, but also significant retention products.
  • Both inversion and retention products originate from the same transition state.
  • Dynamic trajectories accurately predict the observed experimental product ratios.

Conclusions:

  • The unusual selectivity is attributed to the dynamically retained non-equivalence of newly formed and pre-existing bonds after the initial bond migration.
  • Reaction dynamics play a critical role in dictating stereochemical outcomes.
  • This study provides insights into controlling selectivity in complex organic transformations.