Reaction of Alkynyl(phenyl)(p-phenylene)bisiodonium Ditriflates with Nucleophiles. High Reactivity of the Alkynyl Component.

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  • Kitamura Tsugio
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36
  • Fukuoka Takahiro
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36
  • Zheng Lei
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36
  • Fujimoto Takeshi
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36
  • Taniguchi Hiroshi
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36
  • Fujiwara Yuzo
    Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University 36

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Other Title
  • Reaction of Alkynyl phenyl p phenylene
  • Reaction of Alkynyl(phenyl)(<i>p</i>-phenylene)bisiodonium Ditriflates with Nucleophiles. High Reactivity of the Alkynyl Component

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Abstract

Reaction of alkynyl(p-phenylene)bisiodonium ditriflates with potassium thiocyanate in DMF gave alkynyl thiocyanates and p-iodophenyl(phenyl)iodonium triflate. The latter was readily removed by washing with water. The exclusive sulfur attack of thiocyanate ion suggests that the alkynyl group behaves as a soft acceptor of nucleophiles. The reactions with the enolate anion of 2-phenyl-1,3-indandione in DMF afforded 2-(1-cyclopentenyl)-2-phenyl-1,3-indandiones in the cases of 1-hexynyl- and 1-octynyl-(p-phenylene)bisiodonium ditriflates. In the reactions of 3,3-dimethyl-1-butynyl-, phenylethynyl-, and trimethylsilylethynyl-(p-phenylene)bisiodonium ditriflates, 2-alkynyl-2-phenyl-1,3-indandiones were obtained. The same reactions with the enolate anion of 2-phenyl-1,3-indandione in a mixed solvent of 2-methyl-2-propanol and THF improved the yields of the 1-cyclopentenyl- and alkynyl-substituted indandiones. A large difference in the reaction pathways between the (p-phenylene)bisiodonio and phenyliodonio moieties was observed in the sterically hindered 3,3-dimethyl-1-butynyl systems.

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