The University of Southampton
University of Southampton Institutional Repository

Chemical consequences of the mechanical bond: a tandem active template-rearrangement reaction

Chemical consequences of the mechanical bond: a tandem active template-rearrangement reaction
Chemical consequences of the mechanical bond: a tandem active template-rearrangement reaction
We report the unexpected discovery of a tandem active template CuAAC‐rearrangement process in which N2 is extruded en route to the 1,2,3‐triazole product to give instead acrylamide rotaxanes. Mechanistic investigations suggest this process is dictated by the mechanical bond, which stabilizes the CuI‐triazolide intermediate of the CuAAC reaction and diverts it down the rearrangement pathway; when no mechanical bond is formed, the CuAAC product is isolated.
1433-7851
1-6
Modicom, Florian
4dbe5553-a5b4-4431-ae8c-8c19a39c0d48
Jamieson, Ellen Mary Gillies
acaaf8c7-a2a0-446a-9679-9a7ebdfb4e09
Rochette, Elise
fbd3ec59-906e-4ea8-8ad7-fe5b820854a4
Goldup, Stephen Michael
0a93eedd-98bb-42c1-a963-e2815665e937
Modicom, Florian
4dbe5553-a5b4-4431-ae8c-8c19a39c0d48
Jamieson, Ellen Mary Gillies
acaaf8c7-a2a0-446a-9679-9a7ebdfb4e09
Rochette, Elise
fbd3ec59-906e-4ea8-8ad7-fe5b820854a4
Goldup, Stephen Michael
0a93eedd-98bb-42c1-a963-e2815665e937

Modicom, Florian, Jamieson, Ellen Mary Gillies, Rochette, Elise and Goldup, Stephen Michael (2019) Chemical consequences of the mechanical bond: a tandem active template-rearrangement reaction. Angewandte Chemie International Edition, 1-6. (doi:10.1002/anie.201813950).

Record type: Article

Abstract

We report the unexpected discovery of a tandem active template CuAAC‐rearrangement process in which N2 is extruded en route to the 1,2,3‐triazole product to give instead acrylamide rotaxanes. Mechanistic investigations suggest this process is dictated by the mechanical bond, which stabilizes the CuI‐triazolide intermediate of the CuAAC reaction and diverts it down the rearrangement pathway; when no mechanical bond is formed, the CuAAC product is isolated.

Text
Modicom et al 2019 Angewandte Chemie International Edition - Accepted Manuscript
Download (4kB)

More information

Accepted/In Press date: 28 December 2018
e-pub ahead of print date: 2 January 2019
Published date: 14 February 2019

Identifiers

Local EPrints ID: 427437
URI: http://eprints.soton.ac.uk/id/eprint/427437
ISSN: 1433-7851
PURE UUID: 0bb20932-84e7-4af9-b616-6a32ef5bebba
ORCID for Stephen Michael Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 16 Jan 2019 17:30
Last modified: 15 Sep 2021 04:57

Export record

Altmetrics

Contributors

Author: Florian Modicom
Author: Ellen Mary Gillies Jamieson
Author: Elise Rochette

University divisions

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.

×