Acyl cyanide. V. The synthesis of 1-cyano-1-alkenyl esters by the reaction of acyl cyanides with acid anhydrides and isocyanates.
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概要
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The reactions of enolizable acyl cyanides (acetyl, propionyl, and isobutyryl cyanide) with acid anhydrides (acetic, propionic, butyric, isobutyric, and benzoic anhydride) in the presence of a catalytic amount of tertiary amines (pyridine, lutidines, 4-(dimethylamino)pyridine) produced the corresponding 1-cyano-1-alkenyl carboxylates. In the reactions of propionyl cyanide, (<I>Z</I>)-1-cyano-1-propenyl carboxylates were formed predominantly over the (<I>E</I>)-isomers (isomer ratios <I>Z</I>⁄<I>E</I> were <I>ca.</I> 80/20). The reactions of the cyanides with isocyanates also gave the corresponding 1-cyano-1-alkenyl carbamates in moderate yields, and the acid-treatments of 1-cyano-2-methyl-1-propenyl phenylcarbamate induced its annelation into 3-phenyl-1,3-oxazolidine-2,4-dione derivatives.
- 公益社団法人 日本化学会の論文
著者
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Oku Akira
Department Of Chemistry And Materials Technology Kyoto Institute Of Technology
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Imai Hideki
Department of Chemistry, Kyoto Institute of Technology
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Nakaoji Shigeru
Department of Chemistry, Kyoto Institute of Technology
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Kadono Toshio
Department of Chemistry, Kyoto Institute of Technology
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