Intramolecular 1,3-dipolar cycloaddition of nitrile N-oxide accompanied by dearomatization.
Intramolecular 1,3-dipolar cycloaddition of 2-phenoxybenzonitrile N-oxides to benzene rings, accompanied by dearomatization, formed the corresponding isoxazolines in high yields. The X-ray single-crystal structure analysis revealed that the reaction formed the cis-adduct as a single isomer. The substituents on the benzene rings markedly affected the reaction rate, yield, and structure of the final product.
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 (H-126), Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
Morio
M
Yonekawa
Yasuhito
Y
Koyama
Shigeki
S
Kuwata
Toshikazu
T
Takata