Mechanistic study of in situ generation and use of methanesulfonyl azide as a diazo transfer reagent with real-time monitoring by FlowNMR

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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


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