Three Component Reaction of Arynes with Cyclic Ethers and Active Methines: Synthesis of. OMEGA.-Trichloroalkyl Phenyl Ethers

…, H Hino, N Matsunaga, N Nagahora, K Shioji…

Index: Okuma, Kentaro; Fukuzaki, Yuta; Nojima, Akiko; Sou, Ayumi; Hino, Haruna; Matsunaga, Nahoko; Nagahora, Noriyoshi; Shioji, Kosei; Yokomori, Yoshinobu Bulletin of the Chemical Society of Japan, 2010 , vol. 83, # 10 p. 1238 - 1247

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Citation Number: 9

Abstract

Synthesis of ω-chlorinated alkyl phenyl ethers by tandem reaction of arynes with cyclic ethers and active methines was achieved. Reaction of benzenediazonium 2-carboxylate with tetrahydropyran or tetrahydrofuran in refluxing chloroform afforded 6, 6, 6-trichlorohexyl phenyl ether or 5, 5, 5-trichloropentyl phenyl ether in 40% and 61% yields, respectively. When dichloroacetonitrile was used as a reactant, 5, 5-dichloro-5-cyanopentyl phenyl ...