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...

Descripción completa

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
_version_ 1784619462808305664
author Seylar, Joshua
Stasiouk, Dmytro
Simone, Davide L.
Varshney, Vikas
Heckler, James E.
McKenzie, Ruel
author_facet Seylar, Joshua
Stasiouk, Dmytro
Simone, Davide L.
Varshney, Vikas
Heckler, James E.
McKenzie, Ruel
author_sort Seylar, Joshua
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8694910
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-86949102022-04-13 Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency Seylar, Joshua Stasiouk, Dmytro Simone, Davide L. Varshney, Vikas Heckler, James E. McKenzie, Ruel RSC Adv Chemistry 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. The Royal Society of Chemistry 2021-02-05 /pmc/articles/PMC8694910/ /pubmed/35423190 http://dx.doi.org/10.1039/d0ra10619d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Seylar, Joshua
Stasiouk, Dmytro
Simone, Davide L.
Varshney, Vikas
Heckler, James E.
McKenzie, Ruel
Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title_full Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title_fullStr Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title_full_unstemmed Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title_short Breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
title_sort breaking the bottleneck: stilbene as a model compound for optimizing 6π e(−) photocyclization efficiency
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694910/
https://www.ncbi.nlm.nih.gov/pubmed/35423190
http://dx.doi.org/10.1039/d0ra10619d
work_keys_str_mv AT seylarjoshua breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency
AT stasioukdmytro breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency
AT simonedavidel breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency
AT varshneyvikas breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency
AT hecklerjamese breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency
AT mckenzieruel breakingthebottleneckstilbeneasamodelcompoundforoptimizing6pephotocyclizationefficiency

Ejemplares similares