Preparation and Rearrangement of Alkyl and Allyl N-Arylformimidates

o-phenetidine, o-chloroaniline, p-chloroaniline, 2,5-xylidine, 2,4-xylidine have been condensed with ethyl orthoformate to furnish the corresponding formimidates(I). The latter have been rearranged to for­manilides (II). Compounds of type (II) have been transformed to the secondary amines by acid hydrolysis and to tertiary amines by LiAIH₄. Trans-esterification of (I) with allyl alcohol provides the corresponding allyl formimidates which are similarly rearranged, hydrolysed and reduced.