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Communication | Regular issue | Vol 57, No. 10, 2002, pp.1781-1786
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9564
Palladium Catalyzed Double Substitution Reactions of Iodophenol and Iodoaniline Derivatives with Homo-conjugated Compounds to Form Cyclic Ether and Cyclic Amines through Homo-conjugated Interaction

Katsuhiro Saito,* Katsuhiko Ono, Makiko Sano, Shingo Kiso, and Toshihumi Takeda

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

Abstract

Palladium(II) acetate catalyzed double substitution reaction of a bicyclo[2.2.2]octadiene derivative (1) with o-substituted iodobenzenes afforded six membered cyclic compounds (3b and 3c) via a homo-conjugation type interaction accompanied by a five-membered cyclic compound (4a). On the other hand, a similar type of reaction but using a bicyclo[2.2.1]heptadiene derivative (5) formed only the corresponding five-membered cyclic compound (6a).