New mononitromononitriles

Abstract

New g -mononitromononitriles are prepared by condensing a substituted or unsubstituted secondary nitro-paraffin with an unsaturated nitrile having an ethylenic linkage in the a : b - or b : g -position to the CN group, in the presence of a basic substance, for example, an alkali metal hydroxide or alkoxide, piperidine, methyltriethylammonium hydroxide or benzyl trimethyl ammonium hydroxide. In the examples: (1) 2-nitro-1-methoxy-1-phenylpropane (prepared by the action of sodium methoxide on 1-phenyl-2-nitropropene-1) is condensed with acrylonitrile in the presence of sodium hydroxide to give 3-nitro-4-methoxy-3-methyl - 4 - phenylvaleronitrile; (2) 2 - nitropropane and acrylonitrile are reacted to give 3 - nitro - 3 - methylvaleronitrile; (3) nitrocyclohexane and acrylonitrile are reacted to give 1-nitro-1-b -cyanoethylcyclohexane; (4) 2-nitro-propane and crotononitrile are reacted to give 3 - nitro - 2 : 3-dimethylvaleronitrile; (5) acrylonitrile and g -nitrodibutyl sulphone (prepared by the action of nitroethane on n-butyl vinyl sulphone are reacted to give 3-nitro-5-n-butanesulphonyl - 3 - methylcapronitrile. Additional specified starting materials are 2-nitrobutane, a - phenyl - cinnamonitrile, cinnamonitrile, allyl cyanide, a - p - bromophenyl - cinnamonitrile and a - phenyl - p - methoxycinnamonitrile (prepared by the action of p-methoxybenzaldehyde on benzyl cyanide in the presence of alkali).

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