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Lewis acid catalyzed cascade reactions of diarylvinylidenecyclopropanes and 1,1,3-triarylprop-2-yn-1-ols or their methyl ethers.

  作者 Shi, Min;Yao, Liang-Feng;  
  选自 期刊  Chemistry-A European Journal;  卷期  2008年14-28;  页码  8725-8731  
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[摘要]The reactions of vinylidenecyclopropanes with 1,1,3-triarylprop-2-yn-1-ols or their Me ethers in the presence of a Lewis acid selectively produce 4-dihydro-lH-cyclopenta[b]naphthalene derivs. or 1,2,3,8-tetrahydrocyclopenta[a]indene derivs. depending on the substituents on the cyclopropane. Good to high yields are obtained under mild conditions. A plausible cascade Meyer-Schuster rearrangement and Friedel-Crafts reaction mechanism has been proposed. Moreover, functionalized methylene-cyclobutene derivs. could also be obtained in moderate to good yields under similar conditions when strongly electron-donating methoxy groups were introduced into the benzene rings of 1,1,3-triarylprop-2-ynyl Me ether.

 
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