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Restriction lift date:2020-05-07
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
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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