Reactions of N, N'-diarylethylenediimines with grignard reagents, phenylisocyanate and succinic anhydride, part III

ABSTRACT

In previous work, it has been reported that cinnamylideneanilines [-C = C-C = N] consumed one mole of Grignard reagents to give the 1,4-adducts. In order to study the effect of substituent on a basic nitrogen atom connected to the terminal carbon atom, in the above conjugated system, we have investigated the reaction of Grignard reagents on N,N'-diarylethylenediimines [la-b]. Thus, treatment of la with benzylmagnesium chloride and/or Ib with benzylmagnesium chloride, p-anisylmagnesium bromide and cyclohexylmagnesium bromide provided the diadducts [IIa-d], via 1,2-addition of 2 moles of the Grignard reagents to the system -N = C-C = N- with the formation of the intermediate magnesium salt which upon acidification and decomposition gave [II]