Oxidative Electrocyclization of Diradicaloids: C-C Bonds for Free or How to Use Biradical Character for π-Extension

Feofanov M, Akhmetov V, Sharapa DI, Amsharov K (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Organic Letters American Chemical Society

DOI: 10.1021/acs.orglett.0c01717

Abstract

Herein, we show that biradical character and appropriate distribution of spin density can be used for synthetic purposes. We demonstrate the rational domino annulation that includes dehydrative π-extension (DPEX) as the initiation step and subsequent oxidative electrocyclizations (EC) promoted by favorable localization of the unpaired electrons enabling up to four C-C bonds formed during the reaction. Contradicting to the Woodward-Hoffmann rules, the reaction proceeds at room temperature, whereas termination occurs when biradical character vanishes.

Authors with CRIS profile

Mikhail Feofanov Lehrstuhl für Organische Chemie II Vladimir Akhmetov Lehrstuhl für Organische Chemie II Konstantin Amsharov

Involved external institutions

Martin-Luther-Universität Halle-Wittenberg (MLU) DE Germany (DE) Karlsruhe Institute of Technology (KIT) DE Germany (DE)

How to cite

APA:

Feofanov, M., Akhmetov, V., Sharapa, D.I., & Amsharov, K. (2020). Oxidative Electrocyclization of Diradicaloids: C-C Bonds for Free or How to Use Biradical Character for π-Extension. Organic Letters. https://doi.org/10.1021/acs.orglett.0c01717

MLA:

Feofanov, Mikhail, et al. "Oxidative Electrocyclization of Diradicaloids: C-C Bonds for Free or How to Use Biradical Character for π-Extension." Organic Letters (2020).

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