Ritter-type reactions of N-chlorosaccharin: a method for the electrophilic diamination of alkenes.
[reaction: see text] N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile beta-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.
Booker-Milburn
Kevin I
KI
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. k.booker-milburn@bristol.ac.uk
Guly
Dominic J
DJ
Cox
Brian
B
Procopiou
Panayiotis A
PA
D000097:Acetonitriles / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001388:Aziridines / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry*; D003500:Cyclization; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D012439:Saccharin / Q000138:chemical synthesis*; D013343:Styrenes / Q000737:chemistry
D000097:Acetonitriles; D000475:Alkenes; D001388:Aziridines; D007093:Imidazoles; D013343:Styrenes; D002713:Chlorine; C033132:aziridine; D012439:Saccharin; C032159:acetonitrile