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.authorLynch, Denis
dc.contributor.authorO'Mahony, Rosella M.
dc.contributor.authorMcCarthy, Daniel G.
dc.contributor.authorBateman, Lorraine M.
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2019-07-18T14:05:23Z
dc.date.available2019-07-18T14:05:23Z
dc.date.issued2019-05-07
dc.date.updated2019-07-18T13:58:38Z
dc.description.abstractThe 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.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationLynch, 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.201900184en
dc.identifier.doi10.1002/ejoc.201900184en
dc.identifier.endpage3580en
dc.identifier.issn1434-193X
dc.identifier.issued22en
dc.identifier.journaltitleEuropean Journal of Organic Chemistryen
dc.identifier.startpage3575en
dc.identifier.urihttps://hdl.handle.net/10468/8205
dc.identifier.volume2019en
dc.language.isoenen
dc.publisherWileyen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo: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
dc.relation.urihttps://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.subjectDiazo compoundsen
dc.subjectFlow chemistryen
dc.subjectReaction mechanismsen
dc.subjectFlowNMRen
dc.titleMechanistic study of in situ generation and use of methanesulfonyl azide as a diazo transfer reagent with real-time monitoring by FlowNMRen
dc.typeArticle (peer-reviewed)en
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