Et3B-Induced Radical Addition of N,N-Dichlorosulfonamide to Alkenes and Pyrrolidine Formation via Radical Annulation
- 19 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (8) , 3246-3250
- https://doi.org/10.1021/jo034043k
Abstract
A highly regioselective radical addition of N,N-dichlorobenzenesulfonamide (dichloramine-B) to 1-alkenes is achieved at −78 °C by the use of triethylborane as a radical initiator. The reaction of 1,3-dienes with N,N-dichlorosulfonamide in the presence of Et3B regioselectively provides N-chloro-N-allylamide derivatives. N-Chloro-N-allylamides thus obtained react with a variety of alkenes to furnish pyrrolidine derivatives in good yields. A radical annulation reaction among N,N-dichlorosulfonamide, 1,3-dienes, and alkenes has been developed.Keywords
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