Abstract
Substitution reactions of chloroisobutyronitriles and chloromethacrylonitriles with sodium methoxide in methanol were studied. The reaction products were isolated by fractional distillation or gas chromatography and their structures confirmed. The main products were saturated ether compounds, i. e., β-methoxyisobutyronitriles, but small quantities of unsaturated ethers, i. e., methoxymethacrylonitriles, were formed in certain cases. 2-Chloromethyl-2, 3-dichloropropionitrile (7), and trans-and cis-3-chloro-2-chloromethyl-acrylonitriles (5a, 5b) gave a common end product, 2-dimethoxymethyl-3-methoxypropionitrile (15), but gave different reaction intermediates. Methyl 2-chloromethyl-2, 3-dichloropropionimidate (18) was obtained from 7 and 2-dimethoxymethylacrylonitrile (16) from 5a and 5b.
