Acids direct 2-styrylcyclobutanone into two distinctly different reaction pathways.
Two structurally distinct carbocycles were selectively obtained by the reactions of 2-(o-styryl)cyclobutanones promoted by ytterbium salts. Treatment of the cyclobutanones with YbCl(3) in 1,4-dioxane at 100 degrees C afforded 2-(2-chloroethyl)naphthalenes. On the other hand, the reaction with Yb(OTf)(3) in chlorobenzene at 130 degrees C gave 9,10-dihydrobenzocycloocten-7(8H)-ones.
Murakami
Masahiro
M
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Japan. murakami@sbchem.kyoto-u.ac.jp
Kadowaki
Sho
S
Fujimoto
Atsushi
A
Ishibashi
Mitsuru
M
Matsuda
Takanori
T