title: Subtle electronic effects in metal-free rearrangement of allenic alcohols.
abstract: A general and stereoselective rearrangement of allenic alcohols to (E,E)-1,3-dien-2-yl triflates and chlorides was developed under metal-free conditions. Subtle electronic effects of the alkyl and aryl substituents on the carbon bearing the hydroxyl group has a profound impact on the reaction rate and efficiency such that vinyl triflates were obtained from electron-deficient substrates and trimethylsilyl triflate whereas vinyl chlorides were generated with an electron-rich substrate and trimethylsilyl chloride.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, United States.
authors.forename: Venkata R
authors.initials: VR
authors.lastname: Sabbasani
authors.forename: Phani
authors.initials: P
authors.lastname: Mamidipalli
authors.forename: Huijie
authors.initials: H
authors.lastname: Lu
authors.forename: Yuanzhi
authors.initials: Y
authors.lastname: Xia
authors.forename: Daesung
authors.initials: D
authors.lastname: Lee