2-Aminopyrrolin 5-ones and aminocyclopropyl isocyanates therefrom

A process for the preparation of bis-(2-aminopyrrolin-5-ones) comprising the nucleophilic addition of a bis-secondary diamine to 2-ethoxypyrroline-5-one in an anhydrous, inert solvent at temperatures ranging from about ambient temperature to about the boiling point of the solvent employed, said secondary amine having the formula RNH-X-NHR' where R and R' are hydrocarbyl substituents containing from 1 to about 12 carbon atoms and are selected from the class consisting of alkyl, aryl, alkaryl, and aralky groups, and X is a substantially rigid bridging unit selected from the group consisting of 1,4-substituted butyne-2, 1,4-substituted trans-butene-2, bis-methyl substituted m-xylene, and said hydrocarbyl substituted derivatives thereof.

Bis-(aminocyclopropyl isocyanates) characterized by the structure ##STR2## where R and R' are hydrocarbyl substituents containing from 1 to about 12 carbon atoms and are selected from the class consisting of alkyl, aryl, alkaryl, and aralkyl groups, and X is a substantially rigid bridging unit selected from the group consisting of 1,4-substituted butyne-2, 1,4-substituted trans-butene-2, bis-methyl substituted m-xylene, bis-methyl substituted p-xylene, and said hydrocarbyl substituted derivatives thereof.

A process for the preparation of bis-(aminocyclopropyl isocyanates) comprising the photochemical rearrangement of bis-(2-aminopyrroline-5-ones) having the structure ##STR3## where R and R' are hydrocarbyl substituents containing from 1 to about 12 carbon atoms and are selected from the class consisting of alkyl, aryl, alkaryl, and aralkyl groups, and X is a substantially rigid bridging unit selected from the group consisting of 1,4-substituted butyne-2, 1,4-substituted trans-butene-2, bis-methyl substituted m-xylene, bis-methyl substituted p-xylene, and said hydrocarbyl substituted derivatives thereof.