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Communication | Regular issue | Vol 53, No. 12, 2000, pp.2601-2606
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8933
Cycloaddition Reaction of Naphtho[b]cyclopropene with Tropone Derivatives under the Presence of Ytterbium Complex to Form Cyclic Ethers or Cyclic Ketones: Solvent Effect of Chloroform and Benzene on the Reaction Path

Katsuhiro Saito,* Shinichi Ando, and Yoji Kondo

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Reactions of naphtho[b]cyclopropene with 2-substituted tropone derivatives in chloroform under the presence of ytterbium complex afforded two types of cyclic ether compounds via a [8π+2σ] type cycloaddition reactions. On the other hand, the similar reactions but using benzene as a solvent proceeded through a [6π+2π] type cycloaddition path to form cyclic ketone compounds.