Novel tandem reaction of benzyne with cyclic ethers and active methines: synthesis of ω-trichloroalkyl phenyl ethers

✍ Scribed by Kentaro Okuma; Yuta Fukuzaki; Akiko Nojima; Kosei Shioji; Yoshinobu Yokomori

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 179 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.03.058

✦ Synopsis

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.