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Et3B-induced radical addition of N,N-dichlorosulfonamide to alkenes and pyrrolidine formation via radical annulation
- Source :
- JOURNAL OF ORGANIC CHEMISTRY. 68(8):3246-3250
- Publication Year :
- 2003
- Publisher :
- AMER CHEMICAL SOC, 2003.
-
Abstract
- A highly regioselective radical addition of N,N-dichlorobenzenesulfonamide (dichloramine-B) to 1-alkenes is achieved at -78 degrees C by the use of triethylborane as a radical initiator. The reaction of 1,3-dienes with N,N-dichlorosulfonamide in the presence of Et(3)B 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.
- Subjects :
- Addition reaction
Nitroxide mediated radical polymerization
Annulation
Organic Chemistry
Triethylborane
Free-radical reaction
Regioselectivity
General Medicine
Chemical synthesis
Medicinal chemistry
Pyrrole derivatives
Pyrrolidine
chemistry.chemical_compound
chemistry
Radical initiator
Organic chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 68
- Issue :
- 8
- Database :
- OpenAIRE
- Journal :
- JOURNAL OF ORGANIC CHEMISTRY
- Accession number :
- edsair.doi.dedup.....3f9a7e9e2727817107e836dcd63d5b5e