title: Synthesis and structure of hypervalent diacetoxybromobenzene and aziridination of olefins with imino-λ3-bromane generated in situ under metal-free conditions.
abstract: Ligand exchange of p-CF(3)C(6)H(4)BrF(2) with acetoxy groups using AcOH and Ac(2)O affords (diacetoxybromo)benzene in a high yield, which undergoes aziridination of alkenes in the presence of TfNH(2) and sulfamate esters in one pot under mild conditions. The aziridination with TfNH(2) proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the intramolecular versions.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan.
authors.forename: Md Mahbubul
authors.initials: MM
authors.lastname: Hoque
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
authors.forename: Norihiro
authors.initials: N
authors.lastname: Tada
authors.forename: Motoo
authors.initials: M
authors.lastname: Shiro
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D001388:Aziridines; D001555:Benzene Derivatives; D006842:Hydrocarbons, Brominated