Abstract
Reactions of methylaluminium compounds, particularly methylaluminium dichloride, with acethonitrile have been studied. The reactions were found to afford methane and aluminium derivatives of two isomeric acetonitrile trimers. These derivatives on hydrolysis give 2-amino-3-cyano-4-imino-2-pentene and 1-cyano-2-amino-4-imino-2-pentene or their oxygenated analogues, depending on prevailing hydrolysis conditions. An excess of acetonitrile over methylaluminium dichloride was found to favour, and a deficit of acetonitrile to inhibit, the elimination of methane. In the latter case, besides methane and acetonitrile trimerization products, a ketimine derivative is formed, which on hydrolysis yields acetone. When dimethylaluminium chloride and trimethylaluminium are used in 1/1 mole ratios with acetonitrile, corresponding ketimine derivatives are obtained in small yields in addtition to methane elimination products. A mechanism for the methane elimination which yields acetonitrile trimerization products is suggested.
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