Ritter-Type Reactions of N-Chlorosaccharin:  A Method for the Electrophilic Diamination of Alkenes

Ritter-Type Reactions of N-Chlorosaccharin:  A Method for the Electrophilic Diamination of Alkenes

N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing...

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Veröffentlicht in:Organic letters 2003-09, Vol.5 (18), p.3313-3315
Hauptverfasser: Booker-Milburn, Kevin I, Guly, Dominic J, Cox, Brian, Procopiou, Panayiotis A
Format: Artikel
Sprache:eng
Schlagworte:
Acetonitriles - chemistry
Alkenes - chemistry
Amination
Aziridines - chemistry
Chlorine - chemistry
Cyclization
Imidazoles - chemistry
Molecular Structure
Saccharin - chemical synthesis
Styrenes - chemistry
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Zusammenfassung:N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035374m