Acids Direct 2-Styrylcyclobutanone into Two Distinctly Different Reaction Pathways

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 YbCl3 in 1,4-dioxane at 100 °C afforded 2-(2-chloroethyl)naphthalenes. On the other hand, the reaction with Yb(OTf)3 in chl...

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Veröffentlicht in:Organic letters 2005-05, Vol.7 (10), p.2059-2061
Hauptverfasser: Murakami, Masahiro, Kadowaki, Sho, Fujimoto, Atsushi, Ishibashi, Mitsuru, Matsuda, Takanori
Format: Artikel
Sprache:eng
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Zusammenfassung:Two structurally distinct carbocycles were selectively obtained by the reactions of 2-(o-styryl)cyclobutanones promoted by ytterbium salts. Treatment of the cyclobutanones with YbCl3 in 1,4-dioxane at 100 °C afforded 2-(2-chloroethyl)naphthalenes. On the other hand, the reaction with Yb(OTf)3 in chlorobenzene at 130 °C gave 9,10-dihydrobenzocycloocten-7(8H)-ones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0506922