title: Tandem Brook Rearrangement/Silicon Polonovski Reaction via Oxidative Generation of Ammonium Ylides.
abstract: A tandem Brook rearrangement/silicon Polonovski reaction has been achieved by in situ generation of ammonium ylides via the oxidation of α-silyl-tertiary amines. Furthermore, we found that the oxidation of N-(1-cyano-1-silyl)methyl-tertiary amines with peracids induced the tandem Brook rearrangement/silicon Polonovski reaction/fragmentation to give formamide derivatives in moderate yields.
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University.
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Shibuya
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Nakago
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University.
authors.forename: Seiichi
authors.initials: S
authors.lastname: Inoue
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University.
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hoshino
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University.
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Honda
mesh_terms: D000588:Amines / Q000737:chemistry*; D064751:Ammonium Compounds / Q000138:chemical synthesis*; D003640:Dealkylation; D005559:Formamides / Q000138:chemical synthesis*; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D012825:Silicon / Q000737:chemistry*
chemical_list: D000588:Amines; D064751:Ammonium Compounds; D005559:Formamides; C031066:formamide; D012825:Silicon
keywords: Brook rearrangement; Polonovski reaction; dealkylation; tandem reaction; tertiary amine N-oxides