Journal article

Authors list: Strauss, MA; Kohrs, D; Ruhl, J; Wegner, HA

Publication year: 2021

Pages: 3866-3873

Journal: European Journal of Organic Chemistry

Volume number: 2021

Issue number: 28

ISSN: 1434-193X

eISSN: 1099-0690

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/ejoc.202100486

Publisher: Wiley

Abstract: 
The detailed understanding of mechanisms is the basis to design new reactions. Herein, we studied the domino bidentate Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction developed in our laboratory computationally as well as by synthetic experiments, to characterize different pathways. A quinodimethane intermediate was identified as key structure, which is the basis for all subsequent transformations: Elimination to an aromatic naphthalene, rearrangement to a dihydroaminonaphthalene and a photo-induced ring opening. These insights allow to optimize the reaction conditions, such as catalytic utilization of amine, as well as to advance new reactions in the future.

Harvard Citation style: Strauss, M., Kohrs, D., Ruhl, J. and Wegner, H. (2021) Mechanistic Study of Domino Processes Involving the Bidentate Lewis Acid Catalyzed Inverse Electron-Demand Diels-Alder Reaction, European Journal of Organic Chemistry, 2021(28), pp. 3866-3873. https://doi.org/10.1002/ejoc.202100486

APA Citation style: Strauss, M., Kohrs, D., Ruhl, J., & Wegner, H. (2021). Mechanistic Study of Domino Processes Involving the Bidentate Lewis Acid Catalyzed Inverse Electron-Demand Diels-Alder Reaction. European Journal of Organic Chemistry. 2021(28), 3866-3873. https://doi.org/10.1002/ejoc.202100486