Highly Selective Thioselenation of Vinylcyclopropanes with a (PhS) 2 −(PhSe) 2 Binary System and Its Application to Thiotelluration
1998; American Chemical Society; Volume: 64; Issue: 1 Linguagem: Inglês
10.1021/jo981053q
ISSN1520-6904
AutoresAkiya Ogawa, Ikuko Ogawa, Ryoichi Obayashi, Keita Umezu, Mikio Doi, Toshikazu Hirao,
Tópico(s)Chemical Synthesis and Reactions
ResumoA 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.
Referência(s)