Synthesis of Cyclobutenoates from Photochemical Rearrangement of α‐Diazo Cyclopropanes and Computational Studies
The ring expansion of α-cyclopropyl diazoacetates into cyclobutenoates upon irradiation at 425 nm was reported. This method allowed an access to a large array of cyclobutenoates as a mixture of regioisomers. The products were isolated in moderate to excellent yields (17% to 75%) and moderate to good regioisomeric ratio (55:45 to 82:18). The synthetic utility of the products was showcased and the mechanism was studied. Thanks to DFT calculations, the formation of two regioisomers was explained as well as the involvement of a singlet state carbene.
Authors
- Thomas Poisson (ORCID: https://orcid.org/0000-0002-0503-9620)
- Claude Y. Legault (ORCID: https://orcid.org/0000-0002-0730-0263)
- Philippe Jubault (ORCID: https://orcid.org/0000-0002-3295-9326)
- Raphaël Dollet
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université de Sherbrooke (CA)
- Normandie Université (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2025-08-28
- DOI
- https://doi.org/10.1002/chem.202502138
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Indian National Science Academy
- Agence Nationale de la Recherche
- Centre National de la Recherche Scientifique
- Université de Rouen
- Normandie Université
- Région Normandie
- Alliance de recherche numérique du Canada