Reaction of dialkyl-substituted alkynes with carbon dioxide catalyzed by nickel(0) complexes. Incorporation of carbon dioxide in alkyne dimers and novel cyclotrimerization of the alkynes.

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概要

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• Ni(cod)<SUB>2</SUB>–Ph<SUB>2</SUB>P(CH<SUB>2</SUB>)<SUB>4</SUB>PPh<SUB>2</SUB> system (cod=1,5-cyclooctadiene) catalyzed the reaction of 3-hexyne, for example, with CO<SUB>2</SUB> to give a CO<SUB>2</SUB> incorporated product, <I>i.e.</I>, tetraethyl-2-pyrone, in a fairly good yield together with novel two cyclotrimers of the alkyne having cyclopentadiene structures, <I>i.e.</I>, pentaethyl-5-(1-propenyl)-1,3-cyclopentadiene and pentaethyl-5-allyl-1,3-cyclopentadiene. The novel two cyclotrimers were formed selectively on Ni(cod)<SUB>2</SUB>–PPh<SUB>3</SUB> system under CO<SUB>2</SUB>, whereas under N<SUB>2</SUB> the main trimer was hexaethylbenzene. A nickelacyclopentadiene intermediate has been proposed for the pyrone formation. The novel two cyclotrimers were also formed on the oligomerization catalyzed by a cationic nickel hydride complex, [HNi(Ph<SUB>2</SUB>PCH<SUB>2</SUB>CH<SUB>2</SUB>PPh<SUB>2</SUB>)<SUB>2</SUB>]OCOCF<SUB>3</SUB>, together with a novel dimer having a methylenecyclobutene structure, <I>i.e.</I>, 1,2,4-triethyl-3-ethylidenecyclobutene. The effect of phosphine added and that of active-hydrogen compounds on the novel oligomerization are mentioned.

• 公益社団法人 日本化学会の論文

著者

• Inoue Yoshio

  Department Of Biomolecular Engineering Graduate School Of Engineering Tohoku University

• Hashimoto Harukichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoko University

• Itoh Yoshio

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Kazama Haruo

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

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