title: Ag(I)-catalyzed regioselective ring-opening of N-tosylaziridine and N-tosylazetidine with S-, O-, and N-nucleophiles and tethered dinucleophiles.
abstract: [Ag(COD)(2)]PF(6) catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).
authors.affiliation: Organometallics & Catalysis Laboratory, Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India.
authors.forename: Milan
authors.initials: M
authors.lastname: Bera
authors.forename: Sanjay
authors.initials: S
authors.lastname: Pratihar
authors.forename: Sujit
authors.initials: S
authors.lastname: Roy
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D004980:Ethane / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011789:Quantum Theory; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D001384:Azetidines; D001388:Aziridines; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D014105:Tosyl Compounds; D012834:Silver; D004980:Ethane