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

…, T Fukuoka, L Zheng, T Fujimoto, H Taniguchi…

Index: Kitamura, Tsugio; Fukuoka, Takahiro; Zheng, Lei; Fujimoto, Takeshi; Taniguchi, Hiroshi; Fujiwara, Yuzo Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 9 p. 2649 - 2654

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Citation Number: 8

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- ...