title: Highly Selective Thioselenation of Vinylcyclopropanes with a (PhS)(2)-(PhSe)(2) Binary System and Its Application to Thiotelluration.
abstract: A novel, highly selective method for introducing organic sulfur, selenium, and tellurium functions into vinylic cyclopropanes has been developed on the basis of the relative reactivities of organic dichalcogenides and chalcogen-centered radicals. Upon irradiation with the light of wavelength over 300 nm, the reaction of vinylcyclopropanes with diphenyl disulfide and diphenyl diselenide proceeds smoothly to provide the corresponding gamma-(selenoethyl)allylic sulfides regioselectively in good yields. Similarly, vinylcyclopropanes undergo regioselective thiotelluration by use of a novel (PhS)(2)-(PhTe)(2) binary system, affording the corresponding ring-opened thiotelluration product in good yields. Furthermore, the scope and limitations of this (PhS)(2)-(PhTe)(2) binary system are discussed.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors.forename: Akiya
authors.initials: A
authors.lastname: Ogawa
authors.forename: Ikuko
authors.initials: I
authors.lastname: Ogawa
authors.forename: Ryoichi
authors.initials: R
authors.lastname: Obayashi
authors.forename: Keita
authors.initials: K
authors.lastname: Umezu
authors.forename: Mikio
authors.initials: M
authors.lastname: Doi
authors.forename: Toshikazu
authors.initials: T
authors.lastname: Hirao