The formation and X-ray crystal structures of novel spiro-aziridine-azetidinones from thermal reactions between 6-diazopenicillanates and aromatic imines

Abstract

The spiro-aziridine-azetidinones (8), (9), (12)–(17) were prepared by heating equimolar amounts of 6-diazopenicillanate (1) and aromatic imines under reflux in chloroform; the structures of the analogues (18) and (19), prepared from cinnamylidene p-methoxyaniline, were established by X-ray diffraction, as was the structure of the monocyclic β-lactams (10) and (11) formed by heating the benzylidene aniline adducts (8) and (9) under reflux in toluene.