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Communication | Special issue | Vol 52, No. 2, 2000, pp.549-552
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S77
Reaction of Aryl Iodide Derivatives with Homoconjugated Compounds in the Presence of Palladium(II) Acetate to Form Hetero Cyclic Compounds

Toshifumi Takeda and Katsuhiro Saito*

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

Abstract

Reaction of phenol with a tricyclo[3.2.2.02,4]nona—6,9—diene derivative in the presence of palladium(II) acetate afforded a cyclic ether compound, which is considered formally derived from the homo Diels-Alder reaction of the tricyclic compound with phenol followed by dehydrogenation reaction. The yield of the cyclic ether compound was improved by a use of 2-iodophenol instead of phenol. The same type of reaction proceeded between the tricyclic compound and 2-iodoaniline to form a cyclic amine derivative.