title: Oxidation of Olefins with Benzeneseleninic Anhydride in the Presence of TMSOTf.
abstract: A new oxidizing system for olefins, consisting of benzeneseleninic anhydride and trimethylsilyl triflate, was studied. The highly reactive benzeneseleninyl cation is presumably formed under these conditions. It has been shown that different products are formed with this species depending on the specific structure of olefin. The 1,1-disubstituted olefins afforded mostly α,β-unsaturated carbonyl compounds. The sterically encumbered tri- or tetrasubstituted olefins yielded 1,2- or 1,4-dihydroxylated products, presumably via four-membered cyclic intermediates.
authors.affiliation: †Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Izabella
authors.initials: I
authors.lastname: Jastrzębska
authors.affiliation: ‡Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warsaw, Poland.
authors.forename: Maja
authors.initials: M
authors.lastname: Morawiak
authors.affiliation: ‡Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warsaw, Poland.|§Institute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warsaw, Poland.
authors.forename: Joanna E
authors.initials: JE
authors.lastname: Rode
authors.affiliation: †Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Seroka
authors.affiliation: †Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Leszek
authors.initials: L
authors.lastname: Siergiejczyk
authors.affiliation: †Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki