Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock

[Image: see text] The mechanism of the 1,2-spin-center shift in carbohydrate systems was studied with a fluorenylcyclopropyl radical clock. The 1,2-rearrangement of the acyl fluorenylcyclopropane group without opening of the cyclopropane ring provides the strongest evidence that the 1,2-spin-center...

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Autores principales: Witt, Collin H., Woerpel, K. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476153/
https://www.ncbi.nlm.nih.gov/pubmed/37606513
http://dx.doi.org/10.1021/acs.joc.3c01069
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author Witt, Collin H.
Woerpel, K. A.
author_facet Witt, Collin H.
Woerpel, K. A.
author_sort Witt, Collin H.
collection PubMed
description [Image: see text] The mechanism of the 1,2-spin-center shift in carbohydrate systems was studied with a fluorenylcyclopropyl radical clock. The 1,2-rearrangement of the acyl fluorenylcyclopropane group without opening of the cyclopropane ring provides the strongest evidence that the 1,2-spin-center shift in carbohydrate systems occurs through a concerted transition state without the intermediacy of a 1,3-dioxolanyl radical.
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spelling pubmed-104761532023-09-05 Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock Witt, Collin H. Woerpel, K. A. J Org Chem [Image: see text] The mechanism of the 1,2-spin-center shift in carbohydrate systems was studied with a fluorenylcyclopropyl radical clock. The 1,2-rearrangement of the acyl fluorenylcyclopropane group without opening of the cyclopropane ring provides the strongest evidence that the 1,2-spin-center shift in carbohydrate systems occurs through a concerted transition state without the intermediacy of a 1,3-dioxolanyl radical. American Chemical Society 2023-08-22 /pmc/articles/PMC10476153/ /pubmed/37606513 http://dx.doi.org/10.1021/acs.joc.3c01069 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Witt, Collin H.
Woerpel, K. A.
Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title_full Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title_fullStr Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title_full_unstemmed Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title_short Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock
title_sort mechanistic studies on the 1,2-spin-center shift in carbohydrate systems with a fluorenylcyclopropyl radical clock
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476153/
https://www.ncbi.nlm.nih.gov/pubmed/37606513
http://dx.doi.org/10.1021/acs.joc.3c01069
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