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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Detalles Bibliográficos
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
Descripción
Sumario:[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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