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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
Available under License University of Southampton Accepted Manuscript Licence.
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Accepted/In Press date: 28 December 2018
e-pub ahead of print date: 2 January 2019
Published date: 14 February 2019
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Identifiers

Local EPrints ID: 427437
URI: http://eprints.soton.ac.uk/id/eprint/427437
DOI: doi:10.1002/anie.201813950
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: 16 Mar 2024 07:29

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Contributors

Author: Florian Modicom
Author: Ellen Mary Gillies Jamieson
Author: Elise Rochette
Author: Stephen Michael Goldup ORCID iD

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