Organic Letters 2005-05-12

Acids direct 2-styrylcyclobutanone into two distinctly different reaction pathways.

Masahiro Murakami, Sho Kadowaki, Atsushi Fujimoto, Mitsuru Ishibashi, Takanori Matsuda

Index: Org. Lett. 10th ed., 7 , 2059-2061, (2005)

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Abstract

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.

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