Tetra-acetylethylene : a new intermediate for synthesising heterocyclic rings

Abstract

Tetra-acetylethylene (I), prepared by oxidation with iodine of the dithallium(I) salt of tetra-acetylethane (II), reacts with hydrazine to give a mixture of 1,4,5,8-tetramethylpyridazino[4,5-d]pyridazine (IV) and 6-amino-1,4,5,7-tetramethylpyrrolo[3,4-d]pyridazine (V). Treatment of compound (I) with hydrochloric or hydrobromic acid yields furan derivatives, whose structures can be established by chemical and spectroscopic methods. Compound (I) gives a Diels–Alder adduct with 2,3-dimethylbutadiene.