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Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols
File(s)
Author(s)
Natho, Philipp
Annie, Rouse
Greenfield, Jake
Allen, Lewis
Andrew, White
Type
Journal Article
Abstract
Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques.
Date Issued
2020-11-20
Date Acceptance
2020-09-21
Citation
Tetrahedron, 2020, 76 (47)
URI
DOI
ISSN
0040-4020
Publisher
Elsevier Ltd.
Journal / Book Title
Tetrahedron
Volume
76
Issue
47
Copyright Statement
© 2020 Elsevier Ltd. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence http://creativecommons.org/licenses/by-nc-nd/4.0/
License URL
Sponsor
Imperial College Trust
Grant Number
N/A
Subjects
Organic Chemistry
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
Publication Status
Published
Article Number
ARTN 131636
Date Publish Online
2020-10-06