4132-19-8Relevant academic research and scientific papers
Three component reaction of arynes with cyclic ethers and active methines: Synthesis of ω-trichloroalkyl phenyl ethers
Okuma, Kentaro,Fukuzaki, Yuta,Nojima, Akiko,Sou, Ayumi,Hino, Haruna,Matsunaga, Nahoko,Nagahora, Noriyoshi,Shioji, Kosei,Yokomori, Yoshinobu
experimental part, p. 1238 - 1247 (2010/12/20)
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 ether was obtained in 61% yield. While benzenediazonium carboxylate did not react with epoxides, reaction of benzyne derived from 2-(trimethylsilyl)phenyl triflate with epoxides afforded 3,3,3-trichloropropyl phenyl ethers in good yields as isomeric mixtures. The reaction of oxetanes with benzyne was also reported.
Novel tandem reaction of benzyne with cyclic ethers and active methines: synthesis of ω-trichloroalkyl phenyl ethers
Okuma, Kentaro,Fukuzaki, Yuta,Nojima, Akiko,Shioji, Kosei,Yokomori, Yoshinobu
, p. 3063 - 3066 (2008/09/20)
The reaction of benzenediazonium carboxylate with chloroform in refluxing tetrahydrofuran afforded 5,5,5-trichloropentyl phenyl ether in 61% yield along with benzoic acid (7%). When dichloroacetonitrile was used as a reactant, 5,5-dichloro-5-cyanopentyl phenyl ether was obtained in 65% yield. Reactive benzyne derived from diazonium carboxylate initially reacted with THF to give a dipole intermediate, which further reacted with chloroform or dichloroacetonitrile to give ring opened products.
