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

Collin H. Witt; K. A. Woerpel

doi:10.1021/acs.joc.3c01069

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

Collin H. Witt, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	12802-12807
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	88
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.3c01069
State	Published - Sep 1 2023

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.3c01069

Cite this

@article{952bff0c4f8845e8bd1142ecffa6fea4,

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

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.",

author = "Witt, {Collin H.} and Woerpel, {K. A.}",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

month = sep,

day = "1",

doi = "10.1021/acs.joc.3c01069",

language = "English (US)",

volume = "88",

pages = "12802--12807",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock

AU - Witt, Collin H.

AU - Woerpel, K. A.

PY - 2023/9/1

Y1 - 2023/9/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85169918077&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85169918077&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.3c01069

DO - 10.1021/acs.joc.3c01069

M3 - Article

AN - SCOPUS:85169918077

SN - 0022-3263

VL - 88

SP - 12802

EP - 12807

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this