Day, Dan, Farmer, Thomas James orcid.org/0000-0002-1039-7684, Sherwood, James Richard orcid.org/0000-0001-5431-2032 et al. (1 more author) (2022) An experimental investigation into the kinetics and mechanism of the aza-Michael additions of dimethyl itaconate. Tetrahedron. 132921. ISSN 0040-4020
Abstract
The aza-Michael addition is a versatile reaction for the modification of α,β-unsaturated carbonyl compounds with amines. The reactivity of dimethyl itaconate as a bio-based Michael acceptor is explored in this work. Through its reactions with piperidine and dibutylamine, it was found that the order of reaction can be changed by the choice of catalyst, solvent, or the concentration of the amine reactant. The effectiveness of catalysts was proportional to their Lewis acidity. Competitive isomerisation of dimethyl itaconate into unreactive regioisomers can be suppressed using low-polarity solvents and lower temperatures. This investigation of the aza-Michael additions of dimethyl itaconate has clarified the possible reaction mechanisms and optimised the protocol, supporting further use of this reaction in small molecule synthesis and modification of polymers.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Author(s). |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EUROPEAN COMMISSION 887398 |
Depositing User: | Pure (York) |
Date Deposited: | 20 Jul 2022 08:30 |
Last Modified: | 05 Feb 2025 00:08 |
Published Version: | https://doi.org/10.1016/j.tet.2022.132921 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1016/j.tet.2022.132921 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:189169 |
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