On the Question of the Course of the Hetero Diels–Alder Reactions Between N-(2,2,2-Trichloroethylidene)Carboxamides and Dicyclohexylcarbodiimide: A New Case of the Stepwise Zwitterionic Cycloaddition Process
The regioselectivity and the molecular mechanism of the Diels-Alder reactions between <i>N</i>-(2,2,2-trichloroethylidene)carboxamides and dicyclohexylcarbodiimide were explored based on the ωB97xd/6-311G(d) (PCM) calculations. It was found that the reaction course is determined by polar local interactions. It is interesting that the most favored reaction channel is realized not via classical single-step Diels-Alder mechanism, but according to the stepwise scheme with the intervention of the zwitterionic intermediate. The details of the electron density redistribution along the reaction coordinate were explained using the ELF technique.
Authors
- Ewa Dresler (ORCID: https://orcid.org/0000-0001-5035-3056)
- Radomir Jasiński (ORCID: https://orcid.org/0000-0001-8555-6793)
- Przemysław Woliński (ORCID: https://orcid.org/0000-0001-5575-2179)
- Karolina Zawadzińska-Wrochniak (ORCID: https://orcid.org/0000-0001-8601-278X)
Institutions
- Cracow University of Technology (PL)
- Radom College (PL)
- Łukasiewicz Research Network - Institute of Heavy Organic Synthesis "Blachownia" (PL)
Publication Details
- Journal
- Molecules
- Published
- 2025-06-21
- DOI
- https://doi.org/10.3390/molecules30132692
- Citations
- 4
- Primary Topic
- Organic Chemistry Cycloaddition Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Infrastruktura PL-Grid
- Academic Computer Centre Cyfronet, AGH University of Science and Technology