Peer-Reviewed Journal Details
Mandatory Fields
Lynch, D;O'Mahony, RM;McCarthy, DG;Bateman, LM;Collins, SG;Maguire, AR
2019
June
European Journal of Organic Chemistry
Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR
Validated
Optional Fields
TAMING HAZARDOUS CHEMISTRY ORGANIC-SYNTHESIS NMR SPECTROSCOPY TECHNOLOGY EXTRACTION EFFICIENT ONLINE TOOL IR
3575
3580
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.
WEINHEIM
1434-193X
10.1002/ejoc.201900184
Grant Details