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

Collin H. Witt, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)12802-12807
Number of pages6
JournalJournal of Organic Chemistry
Volume88
Issue number17
DOIs
StatePublished - Sep 1 2023

ASJC Scopus subject areas

  • Organic Chemistry

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