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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Accepted version
Date
2019-05-07
Authors
Lynch, Denis
O'Mahony, Rosella M.
McCarthy, Daniel G.
Bateman, Lorraine M.
Collins, Stuart G.
Maguire, Anita R.
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Published Version
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.
Description
Keywords
Diazo compounds , Flow chemistry , Reaction mechanisms , FlowNMR
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
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Copyright
© 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.