dc.contributor.author |
Lynch, Denis |
|
dc.contributor.author |
O'Mahony, Rosella M. |
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dc.contributor.author |
McCarthy, Daniel G. |
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dc.contributor.author |
Bateman, Lorraine M. |
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dc.contributor.author |
Collins, Stuart G. |
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dc.contributor.author |
Maguire, Anita R. |
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dc.date.accessioned |
2019-07-18T14:05:23Z |
|
dc.date.available |
2019-07-18T14:05:23Z |
|
dc.date.issued |
2019-05-07 |
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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 |
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dc.identifier.uri |
http://hdl.handle.net/10468/8205 |
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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. |
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dc.format.mimetype |
application/pdf |
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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 |
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dc.subject |
Flow chemistry |
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dc.subject |
Reaction mechanisms |
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dc.subject |
FlowNMR |
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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 |
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dc.date.updated |
2019-07-18T13:58:38Z |
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dc.description.version |
Accepted Version |
en |
dc.internal.rssid |
493288156 |
|
dc.internal.rssid |
490942633 |
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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!! |
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dc.internal.licenseacceptance |
Yes |
en |
dc.internal.IRISemailaddress |
stuart.collins@ucc.ie |
en |
dc.internal.IRISemailaddress |
a.maguire@ucc.ie |
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dc.internal.IRISemailaddress |
denis.lynch@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 |