The University of Southampton
University of Southampton Institutional Repository
Warning ePrints Soton is experiencing an issue with some file downloads not being available. We are working hard to fix this. Please bear with us.

A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans

A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans
A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans
A dichotomy between the additions of organolithiums and lithium amides to cyclobutenediones is described wherein the former give carbonyl addition products while the latter induce ring opening by enone cleavage via O- to C-lithium transfer.
This distinct mode of ring scission gives access to 2-oxobut-3-enamides and tetrasubstituted furans.
1359-7345
Bennett, Ryan
fc2c4590-ad4a-4929-913e-78cb8379f342
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Wilson, Dharyl Charles
a64ee73e-0685-4aee-b96d-a43ec736fe33
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bennett, Ryan
fc2c4590-ad4a-4929-913e-78cb8379f342
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Wilson, Dharyl Charles
a64ee73e-0685-4aee-b96d-a43ec736fe33
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Bennett, Ryan, Sun, Wei, Wilson, Dharyl Charles, Light, Mark and Harrowven, David C. (2021) A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans. ChemComm. (doi:10.1039/D1CC02097H).

Record type: Article

Abstract

A dichotomy between the additions of organolithiums and lithium amides to cyclobutenediones is described wherein the former give carbonyl addition products while the latter induce ring opening by enone cleavage via O- to C-lithium transfer.
This distinct mode of ring scission gives access to 2-oxobut-3-enamides and tetrasubstituted furans.

Text
D1CC02097H - Version of Record
Available under License Creative Commons Attribution.
Download (1MB)

More information

Accepted/In Press date: 5 May 2021
e-pub ahead of print date: 5 May 2021

Identifiers

Local EPrints ID: 449071
URI: http://eprints.soton.ac.uk/id/eprint/449071
ISSN: 1359-7345
PURE UUID: 6a7a4d88-01ea-494f-93cb-dac839fe233d
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 May 2021 16:33
Last modified: 15 May 2021 01:37

Export record

Altmetrics

Contributors

Author: Ryan Bennett
Author: Wei Sun
Author: Dharyl Charles Wilson
Author: Mark Light ORCID iD

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×