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

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 i...

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Detalles Bibliográficos
Autores principales: Seylar, Joshua, Stasiouk, Dmytro, Simone, Davide L., Varshney, Vikas, Heckler, James E., McKenzie, Ruel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694910/
https://www.ncbi.nlm.nih.gov/pubmed/35423190
http://dx.doi.org/10.1039/d0ra10619d
Descripción
Sumario: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.

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