Volume 29, Issue 1
Isocyclic Compounds
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ChemInform Abstract: Rhodium(I)-Catalyzed Successive Double Cleavage of Carbon—Carbon Bonds of Strained Spiro Cyclobutanones.

M. MURAKAMI

M. MURAKAMI

Dep. Synth. Chem. Biol. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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K. TAKAHASHI

K. TAKAHASHI

Dep. Synth. Chem. Biol. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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H. AMII

H. AMII

Dep. Synth. Chem. Biol. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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Y. ITO

Y. ITO

Dep. Synth. Chem. Biol. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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First published: 24 June 2010

Abstract

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ChemInform Abstract

A new tandem sequence is developed in which two C—C bonds are cleaved successively first through the insertion of rhodium and second by β-carbon elimination. Several examples demonstrate the versatility of this transition-metal-mediated bond cleavage. Whereas with (IX) this double cleavage takes place, cyclobutanone (XII) joined by a seven-membered ring or the non-spiro compound (XIII) fails to react.

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