Biphenyl Cyclobutenone Photoelectrocyclizations
Overview
Overview
Journal
J Org Chem
Publisher
American Chemical Society
Specialty
Chemistry
Date
2021 Sep 29
PMID
34586823
Authors
Affiliations
Affiliations
Soon will be listed here.
Abstract
In this work, we demonstrate that readily available conjugated bis-aryl cyclobutenones undergo photoelectrocyclization reactions to give the corresponding dihydrophenanthrene cyclobutanones when exposed to 350 nm light, TFA, and TMSCl. We have also found that cyclobutenone electrocyclizations and cycloreversions are in equilibrium.
References
1.
Hyodo K, Hasegawa G, Oishi N, Kuroda K, Uchida K
. Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions. J Org Chem. 2018; 83(21):13080-13087.
DOI: 10.1021/acs.joc.8b01810.
View
2.
Zhao X, Rainier J
. The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives. Synthesis (Stuttg). 2021; 53(7):1200-1212.
PMC: 8319837.
DOI: 10.1055/s-0040-1706001.
View
3.
Zhao X, Song C, Rainier J
. Stereodivergent Photoelectrocyclization Reactions of Bis-aryl Cycloalkenones: Intercepting Photoelectrocyclization Intermediates with Acid. Org Lett. 2019; 21(21):8611-8614.
PMC: 7041411.
DOI: 10.1021/acs.orglett.9b03214.
View
4.
Qin Q, Luo X, Wei J, Zhu Y, Wen X, Song S
. Acetonitrile Activation: An Effective Two-Carbon Unit for Cyclization. Angew Chem Int Ed Engl. 2019; 58(13):4376-4380.
DOI: 10.1002/anie.201900947.
View
5.
Zhao X, Song C, Rainier J
. Photoelectrocyclization Reactions of Conjugated Cycloalkenones: Scope and Reactivity. J Org Chem. 2020; 85(8):5449-5463.
PMC: 7847264.
DOI: 10.1021/acs.joc.0c00197.
View