THE STRUCTURE AND GRIGNARD REACTION OF THE β-AMINOCROTONONITRILE

Abstract

The ultraviolet absorption spectra of the low and high melting forms of β-aminocrotononitrile (I) provide evidence that both of them possess the same enamine structure. Since the existence of the polymorphic modifications of I must be excluded on the basis of the thermochemical behavior of I, the difference of the two modifications is capable of accounting for cis and trans isomerism, the low melting modification being the cis form, and the high melting modification being the trans form.In the reaction of I with aromatic Grignard reagents β-amino ketones of the type CH3—CO—CH==C(NH2)—R are formed as the main reaction products.The free radical mechanism of the formation of I is postulated.