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On the Stability of Disubstituted Cyclobutenes - A Computational Study
Boris Maryasin1,2, Nuno Maulide1
1Institute of Organic Chemistry University of Vienna Währinger Strasse 38 1090 Vienna Austria.
European Journal of Organic Chemistry
|April 23, 2019
Summary
Computational study reveals a model predicting products from nucleophilic alkylation of bicyclic lactones. The model determines if cyclobutenecarboxylic acids or dienoic acid isomers form, based on the nucleophile used.
Area of Science:
- Organic Chemistry
- Computational Chemistry
Background:
- Electrocyclic reactions are fundamental in organic synthesis.
- Cyclobutenecarboxylic acids and their isomers present unique reactivity.
- Predicting reaction outcomes is crucial for synthetic planning.
Purpose of the Study:
- To computationally investigate the electrocyclic ring-opening of 2-substituted cyclobutenecarboxylic acids.
- To develop a predictive model for the alkylation of bicyclic lactone electrophiles.
Main Methods:
- Density Functional Theory (DFT) calculations were employed.
- Analysis of reaction pathways and transition states.
- Comparison of calculated energies for different products.
Main Results:
- Detailed computational analysis of the ring-opening mechanism.
- A model was proposed to predict the isomeric product distribution.
- The nature of the nucleophile significantly influences the product outcome.
Conclusions:
- The study provides a computational framework for understanding cyclobutenecarboxylic acid formation.
- The developed model aids in controlling the synthesis of specific isomers.
- This work contributes to the rational design of organic reactions.
Keywords:
CyclobutenesDensity functional calculationsReaction mechanismsRing‐openingSubstituent effectsMore Related Videos
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