A transition-metal-free access to heteroaromatic-fused 4-tetralones by the oxidative ring expansion of the cyclobutanol moiety
File(s)
Accepted version
Author(s)
Natho, Philipp
Allen, Lewis Alexander Thomas
White, Andrew JP
Parsons, Philip James
Type
Journal Article
Abstract
Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the outcome of the reaction. Limitations with certain substituents on the cyclobutanol moiety are also described. Further experimental evidence to support our mechanistic understanding is disclosed, and we now preclude the suggested involvement of a primary radical for this transformation.
Date Issued
2019-07-10
Date Acceptance
2019-07-01
Citation
The Journal of Organic Chemistry, 2019, 84 (15), pp.9611-9626
ISSN
0022-3263
Publisher
American Chemical Society (ACS)
Start Page
9611
End Page
9626
Journal / Book Title
The Journal of Organic Chemistry
Volume
84
Issue
15
Copyright Statement
© 2019 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b01290.
Sponsor
Imperial College Trust
Identifier
https://pubs.acs.org/doi/10.1021/acs.joc.9b01290
Grant Number
N/A
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
HYPOIODITE REACTION
REGIOSELECTIVE SYNTHESIS
C-C
CYCLOADDITION
CYCLOALKANOLS
HETEROCYCLES
CHEMISTRY
MECHANISM
ALKENES
PROBES
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
Organic Chemistry
Publication Status
Published
Date Publish Online
2019-07-10