Diacetyl-L-tartaric acid anhydride reacted with aromatic primary amines to yield imides (3g-l) and amides (4a-f). The ortho-substituted aromatic primary amines either with electron donating or withdrawing groups yielded amides, whereas para-substituted amines produced imides. However, meta-substituted aromatic primary amines with electron withdrawing residues afforded amides while electron donating counterparts furnished imides.
Keywords: Diacetyl-L-tartaric acid anhydride, aromatic primary amines, imides, amides