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| dc.contributor.author | Lynch, Denis | |
| dc.contributor.author | O'Mahony, Rosella M. | |
| dc.contributor.author | McCarthy, Daniel G. | |
| dc.contributor.author | Bateman, Lorraine M. | |
| dc.contributor.author | Collins, Stuart G. | |
| dc.contributor.author | Maguire, Anita R. | |
| dc.date.accessioned | 2019-07-18T14:05:23Z | |
| dc.date.available | 2019-07-18T14:05:23Z | |
| dc.date.issued | 2019-05-07 | |
| dc.identifier.citation | Lynch, D., O'Mahony, R. M., McCarthy, D. G., Bateman, L. M., Collins, S. G. and Maguire, A. R. (2019) 'Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR', European Journal of Organic Chemistry, 2019(22), pp. 3575-3580. doi: 10.1002/ejoc.201900184 | en |
| dc.identifier.volume | 2019 | en |
| dc.identifier.issued | 22 | en |
| dc.identifier.startpage | 3575 | en |
| dc.identifier.endpage | 3580 | en |
| dc.identifier.issn | 1434-193X | |
| dc.identifier.uri | http://hdl.handle.net/10468/8205 | |
| dc.identifier.doi | 10.1002/ejoc.201900184 | en |
| dc.description.abstract | The mechanistic pathway by which the hazardous diazo transfer reagent methanesulfonyl azide can be formed in situ, from methanesulfonyl chloride and aqueous sodium azide, has been investigated using real-time reaction monitoring by FlowNMR. In the presence of triethylamine, rapid generation of methanesufonyl azide is observed, via a mechanistic pathway consistent with involvement of a sulfene or methanesulfonyl triethylammonium intermediate. Accordingly, it is possible to generate and use methanesulfonyl azide in a single synthetic step for a diazo transfer process. | en |
| dc.format.mimetype | application/pdf | en |
| dc.language.iso | en | en |
| dc.publisher | Wiley | en |
| dc.relation.uri | https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900184 | |
| dc.rights | © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version an article which has been published in final form in the European Journal of Organic Chemistry: https://doi.org/10.1002/ejoc.201900184. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. | en |
| dc.subject | Diazo compounds | en |
| dc.subject | Flow chemistry | en |
| dc.subject | Reaction mechanisms | en |
| dc.subject | FlowNMR | en |
| dc.title | Mechanistic study of in situ generation and use of methanesulfonyl azide as a diazo transfer reagent with real-time monitoring by FlowNMR | en |
| dc.type | Article (peer-reviewed) | en |
| dc.internal.authorcontactother | Stuart Collins, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: stuart.collins@ucc.ie | en |
| dc.internal.availability | Full text available | en |
| dc.check.info | Access to this article is restricted until 12 months after publication by request of the publisher | en |
| dc.check.date | 2020-05-07 | |
| dc.date.updated | 2019-07-18T13:58:38Z | |
| dc.description.version | Accepted Version | en |
| dc.internal.rssid | 493288156 | |
| dc.internal.rssid | 490942633 | |
| dc.contributor.funder | Science Foundation Ireland
|
en |
| dc.description.status | Peer reviewed | en |
| dc.identifier.journaltitle | European Journal of Organic Chemistry | en |
| dc.internal.copyrightchecked | No !!CORA!! | |
| dc.internal.licenseacceptance | Yes | en |
| dc.internal.IRISemailaddress | stuart.collins@ucc.ie | en |
| dc.internal.IRISemailaddress | a.maguire@ucc.ie | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/
|
en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/
|
en |
