The Reaction of Propargyl Compounds with Carbon Monoxide and Water in the Presence of Iron Carbonyl Catalyst
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概要
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The reaction of propargyl alcohol as well as its acetate and methyl ether with carbon monoxide and water in the presence of ironpentacarbonyl-amine catalyst under oxymethylation conditions proved to proceed at a much faster rate than that of 1-butyn-4-ol, 1-pentyn-5-ol and alkylacetylenes accompanied by elimination of the functional groups at C-3 to give dimethyl methylsuccinate. 3-Methyl-1-butyn-3-ol and 1-ethynylcyclohexanol reacted in a similar manner, but gave mixtures of unsaturated monoesters and diesters, saturated and unsaturated. The faster rate of reaction and the product obtained were interpreted by a scheme involving a concerted attack of hydroirontetracarbonyl anion, HFe(CO)<SUB>4</SUB><SUP>−</SUP>, at the terminal position to split off the group at C-3. The mononuclear hydrido anion was assumed to be an active catalytic species in the reaction on the basis of both the infrared spectra of the catalyst system under the reaction conditions and the efficiency of potassium hydroxide as a base component.
- 公益社団法人 日本化学会の論文
著者
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Wada Fumio
Department Of Endocrinology Faculty Of Medicine Kagawa Medical University
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MATSUDA Tsutomu
Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa University
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