The Reaction of Open-chain Unconjugated Dienes with Palladium Acetate. Dependence of the Products on Disposition of the Two Double Bonds

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概要

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• The reaction of open-chain unconjugated dienes with palladium acetate in acetic acid was investigated with particular reference to the behavior of the two double bonds in the course of the acetoxylation. 1,5-Hexadiene produced 3-acetoxymethylenecyclopentane (64%), but 2,6-octadiene bearing two terminal methyl groups gave open-chain acetoxylated products: 3-acetoxy-1,6-octadiene (46%) and 7-acetoxy-2,5-octadiene (47%). The reactions of 1,6-heptadiene and diallyl ether are found to proceed <I>via</I> abnormal anti-Markovnikov addition to afford <I>cis</I> and <I>trans</I> 1-acetoxy-1,6-heptadienes (63%) and γ-acetoxyallyl allyl ethers (84%), respectively. No participation of the second double bond has been observed in the reaction of 1,7-octadiene. The behaviors of these dienes to palladium acetate can be reasonably explained by assuming the formation of π,σ-palladium species possessing a stable pseudo-six membered ring.

• 公益社団法人 日本化学会の論文

著者

• MATSUDA Tsutomu

  Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa University

• Kikukawa Kiyoshi

  Department Of Biological And Environmental Chemistry Kinki University

• Takagi Makoto

  Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University

• ADACHI Nobuo

  Department of Electrical Engineering, Colorado State University

• Adachi Nobuo

  Department of Organic Synthesis, Faculty of Engineering, Kyushu University

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