title: Mechanistic studies of the allylic rearrangements of alpha-silyloxy allylic silanes to silyloxy vinylic silanes.
abstract: Mechanistic evidence suggests that the Lewis acid-promoted allylic rearrangement of alpha-silyloxy allylic silanes proceeds along an ionic reaction pathway involving a contact ion pair. The driving force for this transformation is alleviation of steric congestion at the allylic position of the alpha-silyloxy allylic silane and stabilization of pi cc by hyperconjugation.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92696-2025, USA.
authors.forename: Angie I
authors.initials: AI
authors.lastname: Kim
authors.forename: Kyle L
authors.initials: KL
authors.lastname: Kimmel
authors.forename: Antonio
authors.initials: A
authors.lastname: Romero
authors.forename: Jacqueline H
authors.initials: JH
authors.lastname: Smitrovich
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D012821:Silanes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
chemical_list: D012821:Silanes