Studies of the Organic Reaction of Metal Carbonyl. V. The Reaction of Cobalt Hydrocarbonyl with Olefin—The Effects of the Reaction Conditions and of the Structure of Olefin

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概要

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• It has been observed that the reaction of 1-olefin with cobalt hydrocarbonyl is remarkably affected by the reaction conditions and by the structure of olefln.<BR>Some functional groups, such as the ester, <I>n</I>-butoxy and phenyl groups, adjacent to a C= C bond increase the reactivity of the C=C bond; the order of the reactivity is <I>n</I>-butyl vinyl ether, 10<SUP>3</SUP>>styrene, 20>ethyl acrylate, 5>pentene-1. (The numbers indicate the relative reactivities, which have been roughly calculated from the gas absorption curve.)<BR>At a relatively low temperature (below 0°C), the α-carbon atom of the C=C bond of all these olefins except pentene-1 is selectively carbonylated; the reaction scheme may be considered to be as follows; suggesting that cobalt hydrocarbonyl is acting as an acid:<BR>(<U>Remark: Graphics omitted.</U>)<BR>However, these acylcobalt carbonyls with the branched structure isomerize to those with the straight one:<BR>(<U>Remark: Graphics omitted.</U>)<BR>A relatively high temperature (25°C) and a nitrogen atmosphere promote this isomerization considerably. The reverse isomerization seems to occur only with difficulty. On the other hand, these olefins mainly give the β-carbon carbonylated product at 25 °C, the formation of which seems to result from the two successive reactions, the carbonylation of the α-carbon atom and the isomerization of the corresponding acylcobalt carbonyl. However, the distribution of the products from pentene-1 is not affected by the reaction temperature.<BR>A relatively high pressure of carbon monoxide is advantageous for this reaction. Under a nitrogen atmosphere, some reaction other than the carbonylation seems to occur very rapidly, consuming a large part of the cobalt hydrocarbonyl used; a nitrogen atmosphere has an inhibitory effect on the carbonylation.

• 社団法人 日本化学会の論文

著者

• Watanabe Yoshihisa

  Department Of Basic Geriatrics Graduate School Of Medical Science Kyoto Prefectural University Of Medicine

• Takegami Yoshinobu

  Department of Fuel Chemistry Faculty of Engineering Kyoto University

• Watanabe Yoshihisa

  Department of Fuel Chemistry Faculty of Engineering Kyoto University

• Takegami Y.

  Department of Fuel Chemistry Faculty of Engineering Kyoto University

• Yokokawa Chikao

  Department of Fuel Chemistry Faculty of Engineering Kyoto University

• Okuda Yasukazu

  Department of Fuel Chemistry Faculty of Engineering Kyoto University

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