Breaking the bottleneck: stilbene as a model compound for optimizing 6π e− photocyclization efficiency

Joshua Seylar; Dmytro Stasiouk; Davide L. Simone; Vikas Varshney; James E. Heckler; Ruel McKenzie

doi:10.1039/D0RA10619D

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Breaking the bottleneck: stilbene as a model compound for optimizing 6π e⁻ photocyclization efficiency†

Joshua Seylar,

^a Dmytro Stasiouk,^b Davide L. Simone,^c Vikas Varshney,

^c James E. Heckler

^cd and Ruel McKenzie

*^a

Author affiliations

* Corresponding authors

^a School of Polymer Science and Polymer Engineering, The University of Akron, Akron, OH, USA
E-mail: rmckenzie@uakron.edu

^b Department of Chemistry, The University of Akron, Akron, OH, USA

^c Materials and Manufacturing Directorate, Air Force Research Laboratory, WPAFB, OH, USA

^d ARCTOS Technology Solutions, Dayton, OH, USA

Abstract

TEMPO was more suitable at photocyclizing stilbene than iodine. As stilbene concentration increased, TEMPO produced a higher yield of phenanthrene at shorter times and significantly reduced the potential for undesired [2+2] cycloadditions. Iodine retarded phenanthrene formation because it promoted isomerization to (E)-stilbene which encouraged [2+2] cycloaddition.

This article is part of the themed collection: 2021 RSC Advances HOT Article Collection

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Article information

DOI: https://doi.org/10.1039/D0RA10619D
Article type: Paper
Submitted: 17 Dec 2020
Accepted: 25 Jan 2021
First published: 05 Feb 2021
This article is Open Access

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RSC Adv., 2021,11, 6504-6508

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Breaking the bottleneck: stilbene as a model compound for optimizing 6π e⁻ photocyclization efficiency

J. Seylar, D. Stasiouk, D. L. Simone, V. Varshney, J. E. Heckler and R. McKenzie, RSC Adv., 2021, 11, 6504 DOI: 10.1039/D0RA10619D

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