title: Ritter-type reactions of N-chlorosaccharin: a method for the electrophilic diamination of alkenes.
abstract: [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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. k.booker-milburn@bristol.ac.uk
authors.forename: Kevin I
authors.initials: KI
authors.lastname: Booker-Milburn
authors.forename: Dominic J
authors.initials: DJ
authors.lastname: Guly
authors.forename: Brian
authors.initials: B
authors.lastname: Cox
authors.forename: Panayiotis A
authors.initials: PA
authors.lastname: Procopiou
mesh_terms: 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
chemical_list: D000097:Acetonitriles; D000475:Alkenes; D001388:Aziridines; D007093:Imidazoles; D013343:Styrenes; D002713:Chlorine; C033132:aziridine; D012439:Saccharin; C032159:acetonitrile